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US4482718A
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Process for the preparation of 2-(thien-2-yl)- and 2-(thien-3-yl)-ethylamine derivatives
Assignee: Sanofi SA
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Filing: 1982-06-29
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Granted: 1984-11-13
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Expires: 2002-06-29
Abstract
Abstract The present invention provides a process for the preparation of 2-(thien-2-yl)- and 2-(thien-3-yl)-ethylamine derivatives of the general formula: ##STR1## in which R 1 , in the 2-, 3-, 4- or 5-position, is a hydrogen or halogen atom, a nitro, carboxyl, cyano or amino group, a linear or branched alkyl or alkoxy radical or a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or polysubstituted, the aminoethyl chain is in the 2- or 3-position, R 2 , R 3 and R 4 , which are the same or different, are hydrogen atoms or heterocyclic or non-heterocyclic aromatic radicals, which are optionally mono- or polysubstituted, and Ar is a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or polysubstituted.
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; C07D333/26; C07D333/30; C07D333/32; C07F9/28; C07F9/30; C07F9/32; C07F9/3205; C07F9/3211; C07F9/38; C07F9/40; C07F9/4003; C07F9/4006; C07F9/4056; C07F9/50; C07F9/5004; C07F9/553; C07F9/576; C07F9/58; C07F9/655; C07F9/65515
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
295 words
Process for the preparation of 2-(thien-2-yl)- and 2-(thien-3-yl)-ethylamine derivatives of the general formula: ##STR49## in which R 1 , in the 2-, 3-, 4- or 5-position, is a hydrogen or halogen atom, a nitro, carboxyl, cyano or amino group, a linear or branched alkyl or alkoxy radical or a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or polysubstituted, the aminoethyl chain is in the 2- or 3-position, R 2 , R 3 and R 4 , which are the same or different, are hydrogen atoms or heterocyclic or non-heterocyclic aromatic radicals, which are optionally mono- or polysubstituted, and Ar is a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or polysubstituted, wherein a compound of the general formula: ##STR50## in which R 3 has the above-given meaning and X and Y, which may be the same or different, are alkyl, alkoxy, aryl, aryloxy, dialkylamino or diarylamino radicals, is condensed with a carbonyl compound of the general formula: ##STR51## in which Ar and R 4 have the above-given meanings, to give a compound of the general formula: ##STR52## in which X, Y, Ar, R 3 and R 4 have the above-given meanings, which is treated with a base of the general formula B.sup.⊖ M.sup.⊕ to give a carbanion of the general formula: ##STR53## in which X, Y, Ar, R 3 and R 4 have the above-given meanings, which is reacted with a carbonyl derivative of the general formula: ##STR54## in which R 1 and R 2 have the above-given meanings, to give the compound of the general formula: ##STR55## in which R 1 , R 2 , R 3 , R 4 and Ar have the above-given meanings, which is treated with a reducing agent to give a compound of general formula (I).
Claim 2
Dependent Claim
295 words
Process for the preparation of 2-(thien-2-yl)- and 2-(thien-3-yl)-ethylamine derivatives of the general formula: ##STR49## in which R 1 , in the 2-, 3-, 4- or 5-position, is a hydrogen or halogen atom, a nitro, carboxyl, cyano or amino group, a linear or branched alkyl or alkoxy radical or a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or polysubstituted, the aminoethyl chain is in the 2- or 3-position, R 2 , R 3 and R 4 , which are the same or different, are hydrogen atoms or heterocyclic or non-heterocyclic aromatic radicals, which are optionally mono- or polysubstituted, and Ar is a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or polysubstituted, wherein a compound of the general formula: ##STR50## in which R 3 has the above-given meaning and X and Y, which may be the same or different, are alkyl, alkoxy, aryl, aryloxy, dialkylamino or diarylamino radicals, is condensed with a carbonyl compound of the general formula: ##STR51## in which Ar and R 4 have the above-given meanings, to give a compound of the general formula: ##STR52## in which X, Y, Ar, R 3 and R 4 have the above-given meanings, which is treated with a base of the general formula B.sup.⊖ M.sup.⊕ to give a carbanion of the general formula: ##STR53## in which X, Y, Ar, R 3 and R 4 have the above-given meanings, which is reacted with a carbonyl derivative of the general formula: ##STR54## in which R 1 and R 2 have the above-given meanings, to give the compound of the general formula: ##STR55## in which R 1 , R 2 , R 3 , R 4 and Ar have the above-given meanings, which is treated with a reducing agent to give a compound of general formula (I).
Claim 3
Dependent Claim
43 words
Process according to claim 1, wherein the condensation reaction of the organophosphorus compound (II) with the carbonyl compound (III), in the case where the latter is a ketone (R 4 not H), is catalysed by the presence of a mineral or organic acid.
Claim 4
Dependent Claim
11 words
Process according to claim 2, wherein the acid is p-toluenesulphonic acid.
Claim 5
Dependent Claim
33 words
Process according to any of the preceding claims, wherein the formation of the carbanion in the presence of a base is carried out at a temperature of from -78° C. to +100° C.
Claim 6
Dependent Claim
36 words
Process according to claim 4, wherein the base used is an alkali metal hydride, an organomagnesium compound, an alkali metal alcoholate, an alkaline earth metal alcoholate, an alkali metal hydroxide or an alkaline earth metal hydroxide.
Claim 7
Dependent Claim
17 words
Process according to claim 4 or 5, wherein the reaction is carried out in an organic solvent.
Claim 8
Dependent Claim
15 words
Process according to claim 6, wherein the organic solvent is tetrahydrofuran, benzene or dimethyl sulphoxide.
Claim 9
Dependent Claim
41 words
Process according to any of claims 4 to 6, wherein the formation of the carbanion is carried out at a temperature which is chosen, as a function of the base, to be on the whole at the bottom of the range.
Claim 10
Dependent Claim
33 words
Process according to any of the preceding claims, wherein the reaction of the carbanion (V) with the carbonyl derivative (VII) is carried out at a temperature of from -78° C. to +100° C.
Claim 11
Dependent Claim
24 words
Process according to any of the preceding claims, wherein the hydrogenation reaction of the compound (III) is carried out with an alkali metal borohydride.
Claim 12
Dependent Claim
16 words
Process according to claim 10, wherein the alkali metal borohydride is sodium borohydride or potassium borohydride.
Claim 13
Dependent Claim
17 words
Process according to claim 10 or 11, wherein the reaction is carried out in an organic solvent.
Claim 14
Dependent Claim
15 words
Process according to claim 12, wherein the organic solvent is tetrahydrofuran, dioxan, methanol or ethanol.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-11-13 | 1988-05-14 | 1988-11-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-11-13 | 1992-05-14 | 1992-11-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-11-13 | 1996-05-14 | 1996-11-13 | $7700.00 | Window Closed / Lapsed |