GB883220A - Improvements in or relating to morpholine derivatives - Google Patents
Improvements in or relating to morpholine derivativesInfo
- Publication number
- GB883220A GB883220A GB2210859A GB2210859A GB883220A GB 883220 A GB883220 A GB 883220A GB 2210859 A GB2210859 A GB 2210859A GB 2210859 A GB2210859 A GB 2210859A GB 883220 A GB883220 A GB 883220A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- acid addition
- morpholine
- dextrorotatory
- diethanolamine
- 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
- 150000002780 morpholines Chemical class 0.000 title abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 2
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- 229910015900 BF3 Inorganic materials 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 239000012024 dehydrating agents Substances 0.000 abstract 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 229940101209 mercuric oxide Drugs 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises dextrorotatory morpholine derivatives of the general formula <FORM:0883220/IV (b)/1> and their acid addition salts containing pharmaceutically acceptable anions wherein R is a cyclohexyl or a phenyl group, R1 is a C1-5 alkyl R2 is a hydrogen atom or a C1-5 alkyl group, and the substituents R1 and R2 are in threo configuration with respect to one another, and a process for the preparation of both racemic and optically active morpholines of above general formula by heating an acid addition salt of a racemic or optically active diethanolamine of the general formula <FORM:0883220/IV (b)/2> with zinc chloride and separating from the reaction mass the morpholine derivative formed or an acid addition salt thereof. A small quantity of phosphorus pentoxide may be used as an auxiliary dehydrating agent. A laevorotatory diethanolamine is cyclised to form a dextrorotatory morpholine. The diethanolamines above, used as starting materials, are prepared by adding R.CH(OH).C:H to boron trifluoride containing red mercuric oxide to form the corresponding 1,4-dioxane of the formula <FORM:0883220/IV (b)/3> opening the ring, without isolation of the compound, by boiling with hydrochloric acid, hydrogenating the ketol and aminating it with a salt of an aminoalcohol H2NCH2CH2COH) and where R2 is an alkyl group, alkylating the product so obtained. Specification 773,780, U.S.A. Specifications Re-issue 615,488 and 2,835,669, and German Specifications 95,854 and 844,006 are referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2210859A GB883220A (en) | 1959-06-26 | 1959-06-26 | Improvements in or relating to morpholine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2210859A GB883220A (en) | 1959-06-26 | 1959-06-26 | Improvements in or relating to morpholine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB883220A true GB883220A (en) | 1961-11-29 |
Family
ID=10174026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2210859A Expired GB883220A (en) | 1959-06-26 | 1959-06-26 | Improvements in or relating to morpholine derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB883220A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2325647A1 (en) * | 1975-09-27 | 1977-04-22 | Basf Ag | PROCESS FOR PREPARING N-SUBSTITUTED TETRAHYDRO-1,4-OXAZINES |
| EP0094565A3 (en) * | 1982-05-13 | 1984-01-11 | Basf Aktiengesellschaft | Process for the preparation of cis-2,6-dimethyl morpholine |
| WO2011146850A1 (en) * | 2010-05-21 | 2011-11-24 | Research Triangle Institute | Phenylmorpholines and analogues thereof |
| US8906908B2 (en) | 2010-05-21 | 2014-12-09 | Research Triangle Institute | Hydroxybupropion analogues for treating drug dependence |
-
1959
- 1959-06-26 GB GB2210859A patent/GB883220A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2325647A1 (en) * | 1975-09-27 | 1977-04-22 | Basf Ag | PROCESS FOR PREPARING N-SUBSTITUTED TETRAHYDRO-1,4-OXAZINES |
| EP0094565A3 (en) * | 1982-05-13 | 1984-01-11 | Basf Aktiengesellschaft | Process for the preparation of cis-2,6-dimethyl morpholine |
| WO2011146850A1 (en) * | 2010-05-21 | 2011-11-24 | Research Triangle Institute | Phenylmorpholines and analogues thereof |
| US8906908B2 (en) | 2010-05-21 | 2014-12-09 | Research Triangle Institute | Hydroxybupropion analogues for treating drug dependence |
| US9527823B2 (en) | 2010-05-21 | 2016-12-27 | Research Triangle Institute | Hydroxybupropion analogues for treating drug dependence |
| US9617229B2 (en) | 2010-05-21 | 2017-04-11 | Research Triangle Institute | Phenylmorpholines and analogues thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES383503A1 (en) | 1,1,1-trichloro-2-amido-2-amino-ethanes | |
| GB913866A (en) | Improvements in or relating to amino-norcamphane compounds | |
| GB883220A (en) | Improvements in or relating to morpholine derivatives | |
| GB1090304A (en) | Novel phenanthridine derivatives and a process for the manufacture thereof | |
| ES390163A1 (en) | Procedure for the preparation of amino-derivatives of pirazolo (3,4-b) pyridine-5-carboxylic acids. (Machine-translation by Google Translate, not legally binding) | |
| GB933504A (en) | New piperidine derivatives and methods for preparing the same | |
| GB869978A (en) | Method of producing n-alkyl-and-cycloalkyl-piperidine carboxylic acid amides | |
| ES448629A1 (en) | Benzoxazole derivatives, process for their preparation and their use as optical brighteners | |
| GB1061571A (en) | N,n'-disubstituted piperazines and process for their manufacture | |
| GB959203A (en) | Indole derivatives and salts thereof | |
| GB894049A (en) | Method of preparing 10-(1-substituted-3-pyrrolidylmethyl) phenothiazines | |
| GB1064132A (en) | New quinoline derivatives, process for their production and use thereof in the production of carbostyril derivatives | |
| GB907528A (en) | Substituted furfurylamines and tetrahydrofurfurylamines | |
| GB1017450A (en) | 2-amino-4-alkoxy-úË-triazines | |
| GB938646A (en) | New piperazine derivatives | |
| ES396174A1 (en) | Phenylethanolamine derivatives | |
| GB1120310A (en) | Substituted naphthotriazines | |
| ES432465A1 (en) | Substituted 4-biphenylyl-butenoic acids esters and amides and pharmaceutical compositions containing them | |
| GB702847A (en) | Process for the preparation of thienyl substituted tertiary amines | |
| GB827832A (en) | Improvements in or relating to substituted amines | |
| GB873781A (en) | Novel sulphanilamido-pyrimidines and acid addition salts thereof and a process for the manufacture of same | |
| GB932016A (en) | Process for the preparation of boric phenthiazines | |
| GB1004927A (en) | Improvements in or relating to amino-ketones, their preparation and compositions containing them | |
| GB904680A (en) | Process for the production of o-quinones | |
| GB1019462A (en) | Improvements in or relating to novel 3-azabicyclo-[3.2.2]-nonane derivatives |