GB873018A - Substituted phenylcyclopropylamines - Google Patents

Abstract

The invention comprises compounds of the general formula <FORM:0873018/IV (b)/1> (wherein R represents a bromine, chlorine or fluorine atom or a trifluoromethyl group and Z an amino or mono- or di-methylamino group) and their non-toxic pharmaceutically acceptable acid addition salts, and the preparation thereof by the processes of the examples, which may be summarized as follows: an R-substituted styrene is condensed with ethyl diazoacetate to form the correspondingly-substituted ethyl 2-phenylcyclopropanecarboxylate; saponification and separation into cisand trans-isomers follow in either order; the cis- and trans-acids are converted into their azides (preferably via the methyl ester and the hydrazide in the case of the cis-isomer and via the acid chloride in the case of the trans-isomer); the azides are converted into the primary amines of the general formula above (Z = NH2) (preferably via the methylurethane in the case of the cis-isomer and via the isocyanate in the case of the trans-isomer); finally, if desired, the products are monomethylated by reaction with benzaldehyde and treatment of the resulting benzalamine with methyl iodide in a sealed container at 100-105 DEG C., or dimethylated with aqueous formaldehyde and formic acid. The monomethylated compounds can also be prepared by LiAlH4 reduction of the isocyanates or of the N-carbethoxy derivatives obtained by reacting the primary amines with ethyl chloroformate. The products are useful as ataractic, antidepressant and hypotensive agents.