CN111116457A - Green synthesis method of 1,2,2,6, 6-pentamethyl-4-piperidone - Google Patents
Green synthesis method of 1,2,2,6, 6-pentamethyl-4-piperidone Download PDFInfo
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- CN111116457A CN111116457A CN201911368226.6A CN201911368226A CN111116457A CN 111116457 A CN111116457 A CN 111116457A CN 201911368226 A CN201911368226 A CN 201911368226A CN 111116457 A CN111116457 A CN 111116457A
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- piperidone
- pentamethyl
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- GHJUORCGZFHNKG-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidin-4-one Chemical compound CN1C(C)(C)CC(=O)CC1(C)C GHJUORCGZFHNKG-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 238000001308 synthesis method Methods 0.000 title claims abstract description 15
- JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetonamine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 239000002994 raw material Substances 0.000 claims abstract description 10
- 238000001816 cooling Methods 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 8
- 239000012467 final product Substances 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 230000009471 action Effects 0.000 claims abstract description 5
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910021536 Zeolite Inorganic materials 0.000 claims description 6
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 6
- 239000010457 zeolite Substances 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 claims description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract description 10
- 238000000034 method Methods 0.000 abstract description 10
- 238000003756 stirring Methods 0.000 abstract description 7
- 238000003786 synthesis reaction Methods 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract description 5
- 235000019253 formic acid Nutrition 0.000 abstract description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 4
- 231100000331 toxic Toxicity 0.000 abstract description 4
- 230000002588 toxic effect Effects 0.000 abstract description 4
- 239000002351 wastewater Substances 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 230000008569 process Effects 0.000 abstract description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 230000011987 methylation Effects 0.000 description 7
- 238000007069 methylation reaction Methods 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000012022 methylating agents Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 231100000086 high toxicity Toxicity 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- GDJQNGMJGMABLV-UHFFFAOYSA-N 1,3,3,4-tetramethylpiperidin-2-one Chemical compound CC1CCN(C)C(=O)C1(C)C GDJQNGMJGMABLV-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- BCDGQXUMWHRQCB-UHFFFAOYSA-N glycine methyl ketone Natural products CC(=O)CN BCDGQXUMWHRQCB-UHFFFAOYSA-N 0.000 description 1
- 231100000206 health hazard Toxicity 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- -1 methyl halide Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
The invention discloses a green synthesis method of 1,2,2,6, 6-pentamethyl-4-piperidone, which comprises the steps of taking 2,2,6,6-tetramethyl piperidone and DMC as raw materials, stirring and reacting for a certain time at a certain temperature under the action of a solvent and a catalyst, cooling, filtering, concentrating and rectifying under negative pressure after the reaction is finished to obtain a final product 1,2,2,6, 6-pentamethyl-4-piperidone, wherein the yield can reach 90%; the whole synthesis process does not use toxic and harmful dimethyl sulfate, chloroform, methyl iodide, formaldehyde, formic acid and the like, does not discharge waste water in the production process, and is a green synthesis mode of 1,2,2,6, 6-pentamethyl-4-piperidone.
Description
Technical Field
The invention belongs to the technical field of chemical synthesis, and particularly relates to a green synthesis method of 1,2,2,6, 6-pentamethyl-4-piperidone.
Background
The hindered amine light stabilizer HALS is a novel high-efficiency stabilizer, is used for preventing the aging of high polymers such as plastics, rubber and the like, and is the most rapidly developed stabilizer at present. In recent decades, hindered amine light stabilizers have been a very active research area, and new products are continuously emerging. The low-alkalinity alkylation products are a major hotspot in recent years, such as GW-540, Tinuvin 765 of BASF, and = NH on piperidine ring is replaced by = N-R, so that the alkalinity is reduced and the acid resistance is improved.
1,2,2,6, 6-pentamethyl-4-piperidone is an important monomer raw material for methylation, but the industrialization of the 1,2,2,6, 6-pentamethyl-4-piperidone is rarely reported at home and abroad, mainly because the main raw material 2,2,6, 6-tetramethyl-4-piperidone is very sensitive to acid, alkali and heat and is not stable.
Patent EP0729947A1 Process for the methylation of 2,2,6, 6-tetramethylpiperidine-4-one reports a Process for preparing 1,2,2,6, 6-pentamethyl-4-piperidone by reacting 2,2,6, 6-tetramethyl-4-piperidone with formaldehyde and formic acid. The method is a two-step method, wherein in the first step, 2,2,6, 6-tetramethyl-4-piperidone reacts with formaldehyde to generate an imine intermediate, and in the second step, formic acid is added to reduce the intermediate to obtain a product 1,2,2,6, 6-pentamethyl-4-piperidone. The method involves excessive formaldehyde and formic acid, and not only produces a large amount of waste water with high toxicity and difficulty in treatment, but also produces great health hazard to human bodies.
Patent CN 107674019A synthesis method of 1,2,2,6, 6-pentamethyl-4-piperidone reports that 1,2,2,6, 6-pentamethyl-4-piperidone is obtained by ring closing amination reaction of acetone and methylamine serving as raw materials under the action of a catalyst, and the yield can reach about 70 percent at most. However, most of the byproducts are large molecular impurities which can not be recycled, the cost is huge, and industrialization is difficult to realize.
The data also report that the synthesis of 1,2,2,6, 6-pentamethyl-4-piperidone is carried out by taking tetramethylpiperidone as a raw material and dimethyl sulfate as a methylating agent, the yield can reach over 95 percent, although the yield is high, the raw material dimethyl sulfate belongs to a high-risk, highly toxic and highly corrosive medicine, and the waste water generated by using the dimethyl sulfate as the methylating agent has large amount, high toxicity and high salt content, thereby bringing great negative effects to the environment.
Dimethyl carbonate DMC is a green methylating agent, and because of its low toxicity and low environmental impact, it is classified as a non-toxic chemical in Europe in 1992. For this reason, DMC is known as an environmentally friendly methylation feedstock and carbonylation feedstock, and is a methylation chemical that has been introduced and encouraged to replace dimethyl sulfate, methyl halide, and the like, by the chemical industry worldwide.
However, because the DMC methylation condition of dimethyl carbonate is harsh and the catalyst is not suitable, a method for synthesizing 1,2,2,6, 6-pentamethyl-4-piperidone by using dimethyl carbonate is rarely reported at home and abroad.
Therefore, a method for preparing 1,2,2,6, 6-pentamethyl-4-piperidone, which is green, environment-friendly, high in yield and applicable to industrialization, is urgently needed. Relates to a method for synthesizing 1,2,2,6, 6-pentamethyl-4-piperidone by using dimethyl carbonate DMC as a methylation reagent.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims at the problems that the synthesis yield of the 1,2,2,6, 6-pentamethyl-4-piperidone in the prior art is low, or toxic and harmful methylation raw materials are used, and the like, and provides a preparation method of the 1,2,2,6, 6-pentamethyl-4-piperidone, which is green, environment-friendly, efficient, economical and feasible, so as to solve the problems in the prior art.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
1,2,2,6, 6-pentamethyl-4-piperidone, the structural formula is as follows:
as an improvement of the invention, the preparation method comprises the following steps: the method comprises the steps of taking 2,2,6,6-tetramethyl piperidone and dimethyl carbonate (DMC) as raw materials, stirring and reacting for a certain time at a certain temperature under the action of a solvent and a catalyst, cooling, filtering, concentrating and rectifying under negative pressure after the reaction is finished to obtain a final product 1,2,2,6, 6-pentamethyl-4-piperidone, wherein the yield can reach 90%.
Further, the mass of the solvent is 0-5 times of that of 2,2,6,6-tetramethyl piperidone.
Wherein the solvent is one or more of ethanol, isopropanol, acetone, acetonitrile, dimethyl sulfoxide (DMSO), Dimethylformamide (DMF), Dimethylacetamide (DMAC), Hexamethylphosphoramide (HMP), pyridine and nitromethane.
Further, the mass of the catalyst is 0.5-6% of that of 2,2,6,6-tetramethyl piperidone.
Wherein the catalyst is any one or mixture of Y-type zeolite catalyst (such as NaY, KY), 4-Dimethylaminopyridine (DMAP), 1, 5-diazabicyclo [4.3.0] -5-nonene (DBN), 1, 8-diazabicycloundecen-7-ene (DBU), triethylene Diamine (DABCO) and potassium carbonate.
Further, the molar ratio of the 2,2,6, 6-tetramethylpiperidone to the dimethyl carbonate is 1: 1.5-20.
Further, the reaction temperature is 80-160 ℃.
Further, the reaction time is 1 to 10 hours.
Compared with the prior art, the invention has the following beneficial effects because the technology is adopted:
the invention discloses a green synthesis method of 1,2,2,6, 6-pentamethyl-4-piperidone, which comprises the steps of taking 2,2,6,6-tetramethyl piperidone and DMC as raw materials, stirring and reacting for a certain time at a certain temperature under the action of a solvent and a catalyst, cooling, filtering, concentrating and rectifying under negative pressure after the reaction is finished to obtain a final product 1,2,2,6, 6-pentamethyl-4-piperidone, wherein the yield can reach 90%. The whole synthesis process does not use toxic and harmful dimethyl sulfate, chloroform, methyl iodide, formaldehyde, formic acid and the like, does not discharge waste water in the production process, and is a green synthesis mode of 1,2,2,6, 6-pentamethyl-4-piperidone.
Drawings
FIG. 1 is a GC peak spectrum of 1,2,2,6, 6-pentamethyl-4-piperidone prepared in example 4;
FIG. 2 is an MS spectrum of 1,2,2,6, 6-pentamethyl-4-piperidone prepared in example 4 at 5.93 min.
Detailed Description
The present invention will be further illustrated with reference to the following specific embodiments.
Example 1:
adding 100g of 2,2,6,6-tetramethyl piperidone, 300g of dimethyl carbonate and 3g of DBU into a pressure container, stirring and heating to 120 ℃, timing to react for 5 hours, then cooling, filtering, concentrating the filtrate and rectifying under negative pressure to obtain the final product 1,2,2,6, 6-pentamethyl-4-piperidone with the yield of 90%.
Example 2:
adding 110g of 2,2,6,6-tetramethyl piperidone, 260g of dimethyl carbonate, 2.5g of DABCO and 40g of DMF into a pressure vessel, stirring and heating to 110 ℃, reacting for 3 hours while timing, then cooling, filtering, concentrating the filtrate and rectifying under negative pressure to obtain the final product 1,2,2,6, 6-pentamethyl-4-piperidone with the yield of 91%.
Example 3:
adding 80g of 2,2,6,6-tetramethyl piperidone, 200g of dimethyl carbonate, 1g of DABCO and 50g of acetone into a pressure container, stirring and heating to 90 ℃, reacting for 3.5 hours in a timing manner, then cooling, filtering, concentrating the filtrate and rectifying under negative pressure to obtain the final product 1,2,2,6, 6-pentamethyl-4-piperidone with the yield of 89%.
Example 4:
adding 80g of 2,2,6,6-tetramethyl piperidone, 400g of dimethyl carbonate, 1.5g of DBN and 2g of NaY zeolite into a 500ml four-neck flask with a thermometer, installing a condenser tube, stirring and heating to 90 ℃, reacting for 10 hours at a timing, cooling and filtering after the reaction is finished, concentrating and rectifying filtrate to obtain a final product 1,2,2,6, 6-pentamethyl-4-piperidone with the yield of 91%.
The above-mentioned embodiments are merely preferred embodiments of the present invention, and should not be construed as limiting the present invention, and the scope of the present invention should be defined by the claims, and equivalents including technical features of the claims, i.e., equivalent modifications within the scope of the present invention.
Claims (9)
1. A green synthesis method of 1,2,2,6, 6-pentamethyl-4-piperidone is characterized in that: taking 2,2,6,6-tetramethyl piperidone and dimethyl carbonate as raw materials, reacting under the action of a solvent and a catalyst, cooling, filtering, concentrating and rectifying under negative pressure after the reaction is finished to obtain a final product 1,2,2,6, 6-pentamethyl-4-piperidone.
2. The green synthesis method of 1,2,2,6, 6-pentamethyl-4-piperidone as claimed in claim 1, comprising the following steps: the mass of the solvent is 0-5 times of that of 2,2,6,6-tetramethyl piperidone.
3. The green synthesis method of 1,2,2,6, 6-pentamethyl-4-piperidone as claimed in claim 2, comprising the following steps: the solvent is any one or a mixture of more of ethanol, isopropanol, acetone, acetonitrile, dimethyl sulfoxide, dimethylformamide, dimethylacetamide, hexamethylphosphoramide, pyridine and nitromethane.
4. The green synthesis method of 1,2,2,6, 6-pentamethyl-4-piperidone as claimed in claim 1, comprising the following steps: the mass of the catalyst is 0.5-6% of that of 2,2,6,6-tetramethyl piperidone.
5. The green synthesis method of 1,2,2,6, 6-pentamethyl-4-piperidone as claimed in claim 4, comprising the following steps: the catalyst is any one or a mixture of more of a Y-type zeolite catalyst, 4-dimethylaminopyridine, 1, 5-diazabicyclo [4.3.0] -5-nonene, 1, 8-diazabicycloundecene-7-ene, triethylene diamine and potassium carbonate.
6. The green synthesis method of 1,2,2,6, 6-pentamethyl-4-piperidone as claimed in claim 5, comprising the following steps: the Y-type zeolite catalyst is NaY zeolite catalyst or KY zeolite catalyst.
7. The green synthesis method of 1,2,2,6, 6-pentamethyl-4-piperidone as claimed in claim 1, comprising the following steps: the molar ratio of the 2,2,6,6-tetramethyl piperidone to the dimethyl carbonate is 1: 1.5-20.
8. The green synthesis method of 1,2,2,6, 6-pentamethyl-4-piperidone as claimed in claim 1, comprising the following steps: the reaction temperature is 80-160 ℃.
9. The green synthesis method of 1,2,2,6, 6-pentamethyl-4-piperidone as claimed in claim 1, comprising the following steps: the reaction time is 1-10 hours.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0729947A1 (en) * | 1995-03-01 | 1996-09-04 | Ciba-Geigy Ag | Process for the methylation of 2,2,6,6-tetramethylpiperidin-4-one |
| EP0785189A1 (en) * | 1996-01-19 | 1997-07-23 | ENICHEM S.p.A. | Procedure for alkylation of imides |
| CN103073484A (en) * | 2013-01-28 | 2013-05-01 | 山东诚创医药技术开发有限公司 | Preparation method of mepivacaine and optical enantiomer of mepivacaine |
-
2019
- 2019-12-26 CN CN201911368226.6A patent/CN111116457A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0729947A1 (en) * | 1995-03-01 | 1996-09-04 | Ciba-Geigy Ag | Process for the methylation of 2,2,6,6-tetramethylpiperidin-4-one |
| EP0785189A1 (en) * | 1996-01-19 | 1997-07-23 | ENICHEM S.p.A. | Procedure for alkylation of imides |
| CN103073484A (en) * | 2013-01-28 | 2013-05-01 | 山东诚创医药技术开发有限公司 | Preparation method of mepivacaine and optical enantiomer of mepivacaine |
Non-Patent Citations (4)
| Title |
|---|
| MAX THIEL等: "The common effect of elementary sulfur and gaseous ammonia on ketones. XXI. Synthesis and behavior of some 2,6-diphenyl-4-piperidones", 《JUSTUS LIEBIGS ANNALEN DER CHEMIE》 * |
| ULF TILSTAM等: "A Continuous Methylation of Phenols and N,H‑Heteroaromatic Compounds with Dimethyl Carbonate", 《ORGANIC PROCESS RESEARCH & DEVELOPMENT》 * |
| 舒婷，等: "碳酸二甲酯作甲基化试剂的研究进展", 《化工中间体》 * |
| 荣国斌，等: "《高等有机化学》", 31 December 2007 * |
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