Synthesis and pharmacological screening of 1-[2-tert-aminoethyl]-8-fluoro-5-[4-fluorophenyl]-2,3,4,5-tetrahydro-1H-1-benzazepines, their 1-[aminoacetyl] analogues and 1-substituted 9-fluoro-6-[4-fluorophenyl]-5,6-dihydro-4H-s-triazolo[4,3-a]-1-benzazepines

Abstract

7-Fluoro-4-(4-flurophenyl)-1-naphthylamine (III) was identified as a by-product in the transformation of 7-fluoro-4-(4-fluorophenyl)-1-tetralone oxime to the lactam I. Reaction of 8-fluoro-5-(4-flurophenyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (V) with chloracetyl chloride gave the chloramide VI which was treated with secondary amines to give the aminoacetamides VII, VIII, XI and XII. reduction with lithium aluminium hydride afforded the amines IX, X, XIV and XV. Acylation of the piperazinoethanols XII and XV led to the esters XIII, XVI and XVII. Reaction of the lactam I with phosphorus pentasulfide gave the thiolactam II which was treated with a series of acid hydrazides and gave the title compounds XVIII-XXIV. Some of the compounds exhibited only in relatively high doses anticonvulsant and central depressant effects in various tests.