GB702847A - Process for the preparation of thienyl substituted tertiary amines - Google Patents
Process for the preparation of thienyl substituted tertiary aminesInfo
- Publication number
- GB702847A GB702847A GB10147/51A GB1014751A GB702847A GB 702847 A GB702847 A GB 702847A GB 10147/51 A GB10147/51 A GB 10147/51A GB 1014751 A GB1014751 A GB 1014751A GB 702847 A GB702847 A GB 702847A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethylamino
- methylthienyl
- prepared
- hydrochloride salt
- thienylbutane
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Tertiary mono-amines of the general formula <FORM:0702847/IV(b)/1> wherein R1 represents hydrogen or an aryl or aralkyl group or an alkyl group which may contain an alkoxy substituent, R2 and R3 may be the same or different and are alkyl groups containing from 1 to 3 carbon atoms, or the -NR2R3 group represents the morpholino, pyrrolidino or piperidino group, R4 and R5 are thienyl groups or alkyl substituted thienyl groups, and R6 represent hydrogrogen or an alkyl group containing from 1 to 3 carbon atoms, are prepared by hydrogenating compounds of the general formula <FORM:0702847/IV(b)/2> wherein R1, R2, R3, R4 and R5 have the significance indicated above, with metallic sodium in an alcohol (preferably an alcohol having not more than 6 carbon atoms) with or without the presence of water, or in liquid ammonia, or with sodium amalgam and an acid. In the examples the following compounds are prepared: 3-dimethylamino-1:1-di-21-thienylbutane and the hydrochloride and hydrogen oxalate salts, 3-diethylamino-, 3-ethylmethylamino-, 3-pyrrolidino- and 3-morpholino-1:1-di-21-thienylbutane and their hydrochloride salts, 3-piperidino-1:1-di-21-thienylbutane and its hydrogen oxalate salt, 3-dimethylamino- and 3-dimethylamino-2-methyl-1: 1 - di - 21-thienylpropane and their hydrogen oxalate salts, 3-dimethylamino-1:1-di-21-thienylhexane and its hydrochloride salt, 3-dimethylamino-1:1-di-21-(5-methylthienyl) butane and its hydrochloride salt, 3 - dimethylamino - 1 : 1 - di - 21 - (4-methylthienyl) butane, 3-dimethylamino-4-phenyl-1:1-di-21-thienyl-butane and its hydrochloride salt, 3-dimethyl-amino-4-methoxy-1: 1-di-21-thienylbutane and its hydrogen oxalate salt, 3-dimethyl amino-1 - 21 - (5 - methylthienyl) - 1 - 21 - thienylbutane and its hydrochloride salt and 3-dimethylamino - 1 - 21 - (4 - methylthienyl)-1 - 21 - thienylbutane. Specifications 657,301, 702,269 and 702,827 are referred to. 2-Dimethylamino-3-phenylbutyrate is prepared by the addition of dimethylamine to methyl styrylacetate. 2-Dimethylamino-3-methoxybutyrate is prepared by the addition of dimethylamine to methyl 3-methoxycrotonate. 2-b -Dimethylaminobutyrothienone is prepared by the addition of dimethylamine to 2-crotonothienone. 3-Dimethylamino - 1-21-(4-methylthienyl) - 1-21-thienybut-1-ene is prepared by dehydrating the carbinol (the hydrogen oxalate salt is also referred to) obtained from the reaction of 2-(4-methylthienyl) lithium with 2-b -dimethylaminobutyrothienone. The hydrochloride salt is also mentioned. Similarly 3 - Dimethylamino - 1 - 21 - (5 - methylthienyl) - 1-21-thienylbut-1-ene is prepared using 2-(5-methylthienyl) lithium. The hydrochloride salt is also mentioned. 3 - Dimethylamino-1:1-di-21-(5-methylthienyl) - but-1-ene is prepared by the reaction of 2-(5-methylthienyl) lithium and a dimethylamino substituted butyrate and dehydrating the resulting carbinol. The hydrochloride salt is also mentioned. Similarly 3 - Dimethylamino-1:1-di-21-(4 - methylthienyl) but-1-ene is prepared using 2-(4-methylthienyl) lithium. 3 - Dimethylamino - 4 - phenyl 1:1 - di - 21 - thienylbut-1-ene is prepared by the reaction of 2-thienyllithium and methyl 2-dimethylamino-3-phenylbutyrate and dehydrating the resulting carbinol. The hydrochloride salt is also mentioned. Similarly 3 - Dimethylamino - 4 - methoxy - 1 : 1 - di - 21 thienylbut-1-ene is prepared using methyl 2-dimethylamino-3-methoxy-butyrate.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB10147/51A GB702847A (en) | 1950-04-28 | 1950-04-28 | Process for the preparation of thienyl substituted tertiary amines |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB10147/51A GB702847A (en) | 1950-04-28 | 1950-04-28 | Process for the preparation of thienyl substituted tertiary amines |
Publications (1)
Publication Number | Publication Date |
---|---|
GB702847A true GB702847A (en) | 1954-01-27 |
Family
ID=9962374
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB10147/51A Expired GB702847A (en) | 1950-04-28 | 1950-04-28 | Process for the preparation of thienyl substituted tertiary amines |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB702847A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4206213A (en) | 1977-01-12 | 1980-06-03 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler | Dithienylalkylamines and process for their production |
-
1950
- 1950-04-28 GB GB10147/51A patent/GB702847A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4206213A (en) | 1977-01-12 | 1980-06-03 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler | Dithienylalkylamines and process for their production |
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