GB536211A - Manufacture of alkamine esters of di-alicyclic- or aryl-alicyclic-fatty acids - Google Patents
Manufacture of alkamine esters of di-alicyclic- or aryl-alicyclic-fatty acidsInfo
- Publication number
- GB536211A GB536211A GB22279/39A GB2227939A GB536211A GB 536211 A GB536211 A GB 536211A GB 22279/39 A GB22279/39 A GB 22279/39A GB 2227939 A GB2227939 A GB 2227939A GB 536211 A GB536211 A GB 536211A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- esters
- ester
- ethanol
- diethylaminoethanol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000002148 esters Chemical class 0.000 title abstract 8
- 239000000194 fatty acid Substances 0.000 title abstract 7
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- -1 diphenylacetic acid 2-diethylaminoethanol ester Chemical class 0.000 abstract 11
- 150000001408 amides Chemical class 0.000 abstract 5
- AAJLPPDFIRPBDA-UHFFFAOYSA-N 2-cyclohexyl-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)C1CCCCC1 AAJLPPDFIRPBDA-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- RQNOFUZGXHSHOT-UHFFFAOYSA-N 1-(diethylamino)ethanol Chemical class CCN(CC)C(C)O RQNOFUZGXHSHOT-UHFFFAOYSA-N 0.000 abstract 2
- PGGMEZOUAPIYOY-UHFFFAOYSA-N 2,2-dicyclohexylacetic acid Chemical compound C1CCCCC1C(C(=O)O)C1CCCCC1 PGGMEZOUAPIYOY-UHFFFAOYSA-N 0.000 abstract 2
- XQJMXPAEFMWDOZ-UHFFFAOYSA-N 3exo-benzoyloxy-tropane Natural products CN1C(C2)CCC1CC2OC(=O)C1=CC=CC=C1 XQJMXPAEFMWDOZ-UHFFFAOYSA-N 0.000 abstract 2
- QQXLDOJGLXJCSE-UHFFFAOYSA-N N-methylnortropinone Natural products C1C(=O)CC2CCC1N2C QQXLDOJGLXJCSE-UHFFFAOYSA-N 0.000 abstract 2
- QIZDQFOVGFDBKW-DHBOJHSNSA-N Pseudotropine Natural products OC1C[C@@H]2[N+](C)[C@H](C1)CC2 QIZDQFOVGFDBKW-DHBOJHSNSA-N 0.000 abstract 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 2
- 229930195729 fatty acid Natural products 0.000 abstract 2
- 150000004665 fatty acids Chemical class 0.000 abstract 2
- 150000003057 platinum Chemical class 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical group 0.000 abstract 2
- AZZDBAMLOMKUQR-UHFFFAOYSA-N 1-(diethylamino)butan-1-ol Chemical compound CCCC(O)N(CC)CC AZZDBAMLOMKUQR-UHFFFAOYSA-N 0.000 abstract 1
- VBSTXRUAXCTZBQ-UHFFFAOYSA-N 1-hexyl-4-phenylpiperazine Chemical compound C1CN(CCCCCC)CCN1C1=CC=CC=C1 VBSTXRUAXCTZBQ-UHFFFAOYSA-N 0.000 abstract 1
- DZCBKUAAGVVLOX-UHFFFAOYSA-N 1-morpholin-4-ylethanol Chemical compound CC(O)N1CCOCC1 DZCBKUAAGVVLOX-UHFFFAOYSA-N 0.000 abstract 1
- MADORZDTLHDDEN-UHFFFAOYSA-N 1-piperidin-1-ylethanol Chemical compound CC(O)N1CCCCC1 MADORZDTLHDDEN-UHFFFAOYSA-N 0.000 abstract 1
- POLWQCHLQLJPDW-UHFFFAOYSA-N 2,2-dicyclopentylacetic acid Chemical compound C1CCCC1C(C(=O)O)C1CCCC1 POLWQCHLQLJPDW-UHFFFAOYSA-N 0.000 abstract 1
- RCOUBXAMCOEICZ-UHFFFAOYSA-N 2-(1-hydroxyethylamino)ethyl butanoate Chemical compound C(C)CC(=O)OCCNC(C)O RCOUBXAMCOEICZ-UHFFFAOYSA-N 0.000 abstract 1
- MVLIVYYZHZKKQF-UHFFFAOYSA-N 2-(propylamino)propan-2-ol Chemical compound CCCNC(C)(C)O MVLIVYYZHZKKQF-UHFFFAOYSA-N 0.000 abstract 1
- XJJDZZXEHUGAJE-UHFFFAOYSA-N 2-cyclohexyl-2-phenylbutanoic acid Chemical compound C=1C=CC=CC=1C(CC)(C(O)=O)C1CCCCC1 XJJDZZXEHUGAJE-UHFFFAOYSA-N 0.000 abstract 1
- SYUJOANCOQHMKN-UHFFFAOYSA-N 2-cyclohexyl-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C)(C(O)=O)C1CCCCC1 SYUJOANCOQHMKN-UHFFFAOYSA-N 0.000 abstract 1
- AIFSNHHDQGIDIH-UHFFFAOYSA-N 2-cyclohexyl-3-hydroxypropanoic acid Chemical compound OCC(C(O)=O)C1CCCCC1 AIFSNHHDQGIDIH-UHFFFAOYSA-N 0.000 abstract 1
- SFXXYKYOGGWUHX-UHFFFAOYSA-N 2-phenylpentanoic acid Chemical compound CCCC(C(O)=O)C1=CC=CC=C1 SFXXYKYOGGWUHX-UHFFFAOYSA-N 0.000 abstract 1
- PYYBPWSWSPMKTL-UHFFFAOYSA-N 3-(dimethylamino)cyclohexan-1-ol Chemical class CN(C)C1CCCC(O)C1 PYYBPWSWSPMKTL-UHFFFAOYSA-N 0.000 abstract 1
- GOOSAQUYJMBCIV-UHFFFAOYSA-N C(C)OCCCNC(C)O Chemical compound C(C)OCCCNC(C)O GOOSAQUYJMBCIV-UHFFFAOYSA-N 0.000 abstract 1
- XWTYUTWHTOOWSS-MWBPXRJMSA-N Ergonine Natural products O=C(N[C@@]1(CC)C(=O)N2[C@H](C(C)C)C(=O)N3[C@@H]([C@]2(O)O1)CCC3)[C@@H]1C=C2[C@H](N(C)C1)Cc1c3c([nH]c1)cccc23 XWTYUTWHTOOWSS-MWBPXRJMSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- FIMXSEMBHGTNKT-UHFFFAOYSA-N Scopine Natural products CN1C2CC(O)CC1C1C2O1 FIMXSEMBHGTNKT-UHFFFAOYSA-N 0.000 abstract 1
- JACRWUWPXAESPB-QMMMGPOBSA-N Tropic acid Natural products OC[C@H](C(O)=O)C1=CC=CC=C1 JACRWUWPXAESPB-QMMMGPOBSA-N 0.000 abstract 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- UKXSKSHDVLQNKG-UHFFFAOYSA-N benzilic acid Chemical compound C=1C=CC=CC=1C(O)(C(=O)O)C1=CC=CC=C1 UKXSKSHDVLQNKG-UHFFFAOYSA-N 0.000 abstract 1
- 229940087675 benzilic acid Drugs 0.000 abstract 1
- 238000010531 catalytic reduction reaction Methods 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- HQVIMCDEPSJKLO-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(C(=O)NCCN(CC)CC)C1=CC=CC=C1 HQVIMCDEPSJKLO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
536,211. Esters ; amides. SOC. OF CHEMICAL INDUSTRY IN BASLE. Aug. 1, 1939, No. 22279 and 22280. Convention dates, Aug. 5, 1938 and June 20, 1939. [Class 2 (iii)] Alkamine esters of di-alicyclic- or arylalicyclic-fatty acids are prepared by the catalytic hydrogenation of the corresponding diphenyl-fatty acid esters. The products, which may be converted into their quaternary salts, possess therapeutic properties. According to the examples, diphenylacetic acid 2-diethylaminoethanol ester is hydrogenated in presence of activated platinum prepared by reducing platinic oxide and the resulting mixture of the diethylaminoethanol esters of dicyclohexylacetic acid and phenylcyclohexylacetic acid separated ; the former may be converted into its bromallylate, bromomethylate, bromethylate or bromobenzylate, and the latter with its bromomethylate. Other esters specified are the piperidino-ethanol, diethylaminobutanol, morpholino-ethanol, ethylacetoxyethylamino - ethanol, ethyloxypropylamino-ethanol, methylpropylamino-ethanol and m-dimethylaminocyclohexanol esters of phenylcyclohexylacetic acid, the diethylamino-ethanol esters of phenylcyclohexylpropionic acid and phenylcyclohexylbutyric acid, the dicyclohexylacetic acid tropine ester and the α:α-dicyclohexyl-α-oxyacetic acid diethylamino-ethanol ester. Specification 448,181 is referred to. The Specification as open to inspection under Sect. 91 also describes the production of both alkamine esters and amides of alicyclic or arylalicyclic fatty acids by treating with a reducing agent an alkamine ester or amide of a fatty acid containing one or more unsaturated nuclei, followed if desired by the conversion of the product into its quaternary salt. Reference is made to the treatment of. the. alkamine esters and amides of phenyl-fatty acids and naphthalene-fatty acids. An example is present of the conversion of diphenylacetic acid - 2 - diethylaminoethylamide into the corresponding amides first of phenylcyclohexylacetic acid and then of dicyclohexylacetic acid by catalytic hydrogenation in the presence of activated platinum. The following products are also referred to : alkamine esters of dicyclopentylacetic acid, α-cyclohexylhydracrylic acid tropine ester, α-phenyl-α- cyclohexyl-α-oxyacetic acid diethylaminoethanol ester, α-cyclohexylhydracrylic acid scopine ester, α-cyclohexyl-α-propylacetic acid diethylaminoethanol ester, cyclohexylacetic acid diethylaminoethanol ester, phenylcyclohexylacetic acid ergonine methyl ester, phenyl-dimethylaminocyclohexylacetic acid diethylaminoethanol ester and cyclohexyl-diethylaminoethylacetic acid diethylaminoethanol ester. α-Cyclohexylhydracrylic acid and α- cyclohexyl a-propylacetic acid are stated to be obtained by reduction of tropic acid and α- phenyl-α-propylacetic acid respectively with hydrogen in presence of platinum, and α:α- dicyclohexyl-α-oxyacetic acid by catalytic reduction of benzilic acid. Specification 438,659 is referred to in connection with the preparation of the parent materials. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH536211X | 1938-08-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB536211A true GB536211A (en) | 1941-05-07 |
Family
ID=4518783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB22279/39A Expired GB536211A (en) | 1938-08-05 | 1939-08-01 | Manufacture of alkamine esters of di-alicyclic- or aryl-alicyclic-fatty acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB536211A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2474796A (en) * | 1946-01-31 | 1949-06-28 | Wm S Merrell Co | Alkylaminoalkyl esters of alicyclyl-alicyclic carboxylic acids |
-
1939
- 1939-08-01 GB GB22279/39A patent/GB536211A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2474796A (en) * | 1946-01-31 | 1949-06-28 | Wm S Merrell Co | Alkylaminoalkyl esters of alicyclyl-alicyclic carboxylic acids |
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