Hexahydroazepine derivatives, a process for their preparation

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).