Claims
- 1. A process for the preparation of a hexahydroazepine derivative of formula ##STR10## in which: A is a --CH.dbd.CH--(cis) group;
- X represents hydrogen or a halogen;
- Y is a cyclohexyl group or, when X is hydrogen, a phenyl group;
- or of their pharmaceutically acceptable addition salts with mineral or organic acids, wherein:
- a) a condensation reaction is carried out in the presence of heat and an inert solvent with formaldehyde and hexahydroazepine on a phenylacetylene derivative of formula: ##STR11## in which X and Y have the meanings indicated above, to obtain an acetylenic bond containing compound of formula ##STR12## b) a hydrogenation by nascent hydrogen of the acetylenic bond of the acetylenic containing compound is carried out to prepare a compound of formula (l) in which A represents the --CH.dbd.CH-- group in the form of a mixture of cis and trans isomers and said cis isomer is separated from said mixture; or
- c) a hydrogenation is carried out in the presence of a supported metal catalyst to directly prepare the vinylene compound of formula (l) in cis form; and
- d) optionally, an acid addition salt of a compound of formula (l) is prepared by addition of an appropriate mineral or organic acid to the hydrogenation product of step b) or c).
- 2. A process according to claim 1 wherein the condensation reaction is carried out in the presence of a metallic salt catalyst.
- 3. A process according to claim 2 wherein the metallic salt catalyst is cuprous or cupric chloride and the inert solvent is dioxane or dimethoxyethane.
- 4. A process according to claim 1 wherein the supported catalyst is palladium on barium sulphate or on calcium carbonate, or Raney nickel, in an alcoholic solvent and in the presence of quinoline.
- 5. A process according to claim 2 wherein the supported catalyst is palladium on barium sulphate or on calcium carbonate, or Raney nickel, in an alcoholic solvent and in the presence of quinoline.
- 6. A process according to claim 1 wherein the condensation reaction is carried out on the 3-chloro-4-cyclohexyl-1-ethynylbenzene and wherein the cis-3-(hexahydroazepin-1-yl)-1-(3-chloro-4-cyclohexylphenyl)-1-propene is prepared as a free base or as a pharmaceutically acceptable addition salt.
- 7. A process according to claim 6 wherein the cis-3-(hexahydroazepin-1-yl)-1-(3-chloro-4-cyclohexylphenyl)-1-propene is prepared as a hydrochloride.
Priority Claims (1)
Number |
Date |
Country |
Kind |
90 07434 |
Jun 1990 |
FRX |
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Parent Case Info
This application is a division of application Ser. No. 07/714,832, filed Jun. 13, 1991, now U.S. Pat. No. 5,231,092.
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Non-Patent Literature Citations (3)
Entry |
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Divisions (1)
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Number |
Date |
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Parent |
714832 |
Jun 1991 |
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