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US4458086A
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Process for the preparation of 2-(thienyl-2)-and 2-(thienyl-3)-ethylamines
Assignee: Sanofi SA
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Filing: 1982-06-29
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Granted: 1984-07-03
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Expires: 2002-06-29
Abstract
Abstract The present invention provides a process for the preparation of 2-(thienyl-2)- and 2-(thienyl-3)-ethylamines of the general formula: ##STR1## in which R 1 , which is in the 2-, 3-, 4- or 5-position, is a hydrogen atom, a straight-chained or branched alkyl radical or a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or polysubstituted, or R 1 is an alkoxy radical, a halogen atom or a nitro, carboxyl, cyano or amino group; the aminoethyl chain is in the 2- or 3-position of the thiophene nucleus; R 2 is a hydrogen atom or a straight-chained or branched alkyl radical or a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or poly-substituted; and Ar is a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or poly-substituted.
Inventors
- 👤 Isaac Chekroun
- 👤 Alain Heymes
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 22:50
CPC Classifications
C; C07; C07D; C07D409/00; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6553; C07F9/655345; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/14; C07D333/20; C07F9/28; C07F9/38; C07F9/40; C07F9/4003; C07F9/4006
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
363 words
Process for the preparation of 2-(thienyl-2)- and 2-(thienyl-3)-ethylamines of the general formula: ##STR23## in which R 1 , which is in the 2-, 3-, 4- or 5-position, is a hydrogen atom, a straight-chained or branched alkyl radical or a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or polysubstituted, or R 1 is an alkoxy radical, a halogen atom or a nitro, carboxyl, cyano or amino group; the aminoethyl chain is in the 2- or 3-position of the tiophene nucleus; R 2 is a hydrogen atom or a straight-chained or branched alkyl radical or a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or polysubstituted; and Ar is a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or polysubstituted, which comprises the steps of heating a carbanion of the general formula: ##STR24## in which M + is an alkali or alkaline earth metal, X and Y, which may be the same or different, are alkyl, aryl, alkoxy, aryloxy, dialkylamino or diarylamino radicals and R 1 has the same meaning as above, so as to form a compound of the general formula: ##STR25## in which M + R 1 , X and Y have the same meanings as above, treating with water so as to yield, a compound of the general formula: ##STR26## in which R 1 , X and Y have the same meanings as above, reduction of which gives a compound of the general formula: ##STR27## in which R 1 , X and Y have the same meanings as above, reacting the compound formed with a base of the general formula B' - M' + wherein B' - is hydrogen, amide, dialkylamide, alkyl, alkylate or hydroxy, M' + is an alkali or alkaline earth metal, and reacting with a halogen derivative of the general formula: Ar--CHX--R.sub.2 (IX) in which Ar and R 2 have the same meanings as above and X is a halogen atom, to give a compound of the general formula: ##STR28## in which Ar, R 1 , R 2 , X and Y have the same meanings as above, which is finally converted into a compound of general formula (I) by the action of an acid.
Claim 2
Dependent Claim
363 words
Process for the preparation of 2-(thienyl-2)- and 2-(thienyl-3)-ethylamines of the general formula: ##STR23## in which R 1 , which is in the 2-, 3-, 4- or 5-position, is a hydrogen atom, a straight-chained or branched alkyl radical or a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or polysubstituted, or R 1 is an alkoxy radical, a halogen atom or a nitro, carboxyl, cyano or amino group; the aminoethyl chain is in the 2- or 3-position of the tiophene nucleus; R 2 is a hydrogen atom or a straight-chained or branched alkyl radical or a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or polysubstituted; and Ar is a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or polysubstituted, which comprises the steps of heating a carbanion of the general formula: ##STR24## in which M + is an alkali or alkaline earth metal, X and Y, which may be the same or different, are alkyl, aryl, alkoxy, aryloxy, dialkylamino or diarylamino radicals and R 1 has the same meaning as above, so as to form a compound of the general formula: ##STR25## in which M + R 1 , X and Y have the same meanings as above, treating with water so as to yield, a compound of the general formula: ##STR26## in which R 1 , X and Y have the same meanings as above, reduction of which gives a compound of the general formula: ##STR27## in which R 1 , X and Y have the same meanings as above, reacting the compound formed with a base of the general formula B' - M' + wherein B' - is hydrogen, amide, dialkylamide, alkyl, alkylate or hydroxy, M' + is an alkali or alkaline earth metal, and reacting with a halogen derivative of the general formula: Ar--CHX--R.sub.2 (IX) in which Ar and R 2 have the same meanings as above and X is a halogen atom, to give a compound of the general formula: ##STR28## in which Ar, R 1 , R 2 , X and Y have the same meanings as above, which is finally converted into a compound of general formula (I) by the action of an acid.
Claim 3
Dependent Claim
48 words
The process according to claim 1, which comprises using a stoichiometric amount of the base B' - M' + , the compound of the formula (VII) is reacted with the halogen derivative of the formula (IX) and then reduced to give the compound of the formula (X) directly.
Claim 4
Dependent Claim
34 words
Process according to claim 1 or 2, wherein the conversion of the compound of formula (V) into compound of formula (VI) is carried out at a temperature of from -78° C. to +150° C.
Claim 5
Dependent Claim
23 words
Process according to claim 3, wherein the temperature is selected as a function of the base in the upper part of the range.
Claim 6
Dependent Claim
22 words
Process according to any one of claims 1, 2, 3 or 4 wherein the reaction is carried out in an organic solvent.
Claim 7
Dependent Claim
24 words
Process according to claim 5, wherein the solvent is a straight-chained or cyclic ether, an aromatic hydrocarbon, an alcohol, an amide or a sulphoxide.
Claim 8
Dependent Claim
24 words
Process according to any of claims 1, 2, 3, 4, 5 or 6 wherein the reduction is carried out with an alkali metal borohydride.
Claim 9
Dependent Claim
13 words
Process according to claim 7, wherein the borohydride is sodium or potassium borohydride.
Claim 10
Dependent Claim
9 words
Process according to claim 1 wherein 2-(thienyl-3)-ethylamines, are prepared.
Claim 11
Dependent Claim
10 words
The process according to claim 1 wherein 2-(thienyl-2)-ethylamines are prepared.
Claim 12
Dependent Claim
11 words
The process according to claim 1 wherein N-o-chlorobenzyl-2-(thienyl-2)-ethylamine hydrochloride is prepared.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-07-03 | 1988-01-02 | 1988-07-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-07-03 | 1992-01-02 | 1992-07-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-07-03 | 1996-01-02 | 1996-07-03 | $7700.00 | Window Closed / Lapsed |