GB807835A - New tertiary amines and their salts and process for their preparation - Google Patents
New tertiary amines and their salts and process for their preparationInfo
- Publication number
- GB807835A GB807835A GB7467/58A GB746758A GB807835A GB 807835 A GB807835 A GB 807835A GB 7467/58 A GB7467/58 A GB 7467/58A GB 746758 A GB746758 A GB 746758A GB 807835 A GB807835 A GB 807835A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenethyl
- isopropyl
- diethyl
- alkyl
- phenyl
- 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
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
The invention comprises amines of the general formula <FORM:0807835/IV (b)/1> and acid addition and quaternary salts thereof, wherein R is a hydrogen atom or an alkyl or alkoxy group of 1-6 carbon atoms, R1 and R2 are each an alkyl or hydroxyalkyl group of 1-6 carbon atoms or a cycloalkyl or monocyclic aryl group or an alkyl group of 1-6 carbon atoms bearing a monocyclic aryl substituent or NR1R2 together for a heterocyclic ring which may optionally contain a further hetero-atom and Y is a substituted or unsubstituted aralkyl group or an alkyl group of 3-12 carbon atoms. The amines are prepared by treating an aminopropionitrile of the formula <FORM:0807835/IV (b)/2> with an organomagnesium halide of the formula Hal-Mg-Y, in an inert solvent such as ether, dibutyl ether, dioxan, benzene or benzene/tetrahydrofuran, preferably at the boiling-point of the solvent, and hydrolysing the resulting condensation product to give the amine. The products may be converted into their acid addition salts such as the hydrochloride, hydrobromide, sulphate, phosphate, nitrate, acetate, propionate, butyrate, valerate, oxalate, malonate, succinate, maleate, fumarate, lactate, tartrate, citrate, malate, benzoate, phthalate, cinnamate, salicylate, nicotinate or furan-2-carboxylate or into their quaternary salts with alkyl halides, dimethyl sulphate, diethyl sulphate, alkyl p-toluenesulphonates, cyclohexyl halides or cyclopentyl halides. Preferred products include the o -phenyl derivatives of 4-pyrrolidino-pentane, 4-piperidino-pentane, 5-pyrrolidino-hexane, 3-pyrrolidino-2-methylbutane and 1 - phenyl - 3 - dimethylaminobutane. Specified products prepared in the examples include (a) phenethylamines; a -nonyl - N:N - diethyl -, a - benzyl - N:N - di - n - butyl -, a - phenethyl - N:N - dimethyl -, a - (a - phenylethyl) - N:N - diethyl -, a - phenethyl - N:N - diethyl -, a - phenethyl - N:N - di-n-butyl- and a -p-isopropyl-phenethyl-N:N-diethyl-; (b) morpholines; N-[a -(g -phenylpropyl) - p - methylphenethyl] -, N - [a - (b - p - isopropylphenyl - isopropyl) - phenethyl] - an N - a - isopropyl - phenethyl -; (c) piperidines; N - a - (g - phenylpropyl) - phenethyl - and N - a -propyl-phenethyl-, and (d) pyrrolidines; N-[a - (b - p - isopropylphenyl - isopropyl) - phenethyl] -, N - a - propyl - phenethyl -, N - a - butyl - phenethyl -, N - a - isopropyl - phenethyl -, N - a - (a - phenylethyl) - phenethyl -, N - a - phenethyl - phenethyl -, and N - a - benzyl - phenethyl. a - Tertiary - aminopropionitriles of the formula II used as starting materials, such as 2 - phenyl - 1 - piperidino - propionitrile, 2 - phenyl - 1 - diethylamino - propionitrile and 2 - p - methylphenyl - 1 - morpholino - propionitrile are made by known methods, for example by the reaction of an aldehyde such as a phenyl acetaldehyde with potassium cyanide and an amine of the formula NHR1R2. 3 - (4 - Isopropylphenyl) - 2 - methyl - 1 - pyrrolidino - butyronitrile is made by the action of sodium bisulphite, pyrrolidine and potassium cyanide on cyclamen aldehyde.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE807835X | 1955-07-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB807835A true GB807835A (en) | 1959-01-21 |
Family
ID=6722942
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB7467/58A Expired GB807835A (en) | 1955-07-01 | 1955-09-23 | New tertiary amines and their salts and process for their preparation |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB807835A (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996026196A2 (en) * | 1995-02-23 | 1996-08-29 | Schering Corporation | Benzylpiperidines and piperazines as muscarinic antagonists |
US5889006A (en) * | 1995-02-23 | 1999-03-30 | Schering Corporation | Muscarinic antagonists |
WO1999065860A1 (en) * | 1998-06-18 | 1999-12-23 | Merck Patent Gmbh | Method for catalytically disubstituting carboxylic acid amides with at least one grignard reagent |
WO1999065855A2 (en) * | 1998-06-18 | 1999-12-23 | Merck Patent Gmbh | Combinatorial libraries of geminally substituted amines |
WO2001044161A2 (en) * | 1999-12-17 | 2001-06-21 | Merck Patent Gmbh | Method for producing combinatorial libraries of aryl-substituted amines |
WO2001044160A2 (en) * | 1999-12-14 | 2001-06-21 | Merck Patent Gmbh | Method for producing combinatorial amine libraries |
-
1955
- 1955-09-23 GB GB7467/58A patent/GB807835A/en not_active Expired
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6037352A (en) * | 1995-02-23 | 2000-03-14 | Schering Corporation | Muscarinic antagonists |
WO1996026196A3 (en) * | 1995-02-23 | 1996-10-03 | Schering Corp | Benzylpiperidines and piperazines as muscarinic antagonists |
US5889006A (en) * | 1995-02-23 | 1999-03-30 | Schering Corporation | Muscarinic antagonists |
US6498168B2 (en) | 1995-02-23 | 2002-12-24 | Schering Corporation | Muscarinic antagonists |
WO1996026196A2 (en) * | 1995-02-23 | 1996-08-29 | Schering Corporation | Benzylpiperidines and piperazines as muscarinic antagonists |
US6288068B1 (en) | 1995-02-23 | 2001-09-11 | Schering Corporation | Muscarinic antagonists |
US6043255A (en) * | 1995-02-23 | 2000-03-28 | Schering Corporation | Muscarinic antagonists |
WO1999065855A2 (en) * | 1998-06-18 | 1999-12-23 | Merck Patent Gmbh | Combinatorial libraries of geminally substituted amines |
WO1999065318A2 (en) * | 1998-06-18 | 1999-12-23 | Merck Patent Gmbh | Geminally substituted amines |
WO1999065864A2 (en) * | 1998-06-18 | 1999-12-23 | Merck Patent Gmbh | Geminally substituted amines |
US6448445B1 (en) | 1998-06-18 | 2002-09-10 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Method for catalytically disubstituting carboxylic acid amides with at least one grignard reagent |
WO1999065860A1 (en) * | 1998-06-18 | 1999-12-23 | Merck Patent Gmbh | Method for catalytically disubstituting carboxylic acid amides with at least one grignard reagent |
WO1999065318A3 (en) * | 1998-06-18 | 2003-04-17 | Merck Patent Gmbh | Geminally substituted amines |
WO1999065864A3 (en) * | 1998-06-18 | 2003-05-22 | Merck Patent Gmbh | Geminally substituted amines |
WO1999065855A3 (en) * | 1998-06-18 | 2003-12-11 | Merck Patent Gmbh | Combinatorial libraries of geminally substituted amines |
WO2001044160A2 (en) * | 1999-12-14 | 2001-06-21 | Merck Patent Gmbh | Method for producing combinatorial amine libraries |
WO2001044160A3 (en) * | 1999-12-14 | 2002-03-07 | Merck Patent Gmbh | Method for producing combinatorial amine libraries |
WO2001044161A2 (en) * | 1999-12-17 | 2001-06-21 | Merck Patent Gmbh | Method for producing combinatorial libraries of aryl-substituted amines |
WO2001044161A3 (en) * | 1999-12-17 | 2002-04-11 | Merck Patent Gmbh | Method for producing combinatorial libraries of aryl-substituted amines |
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