Studies on Psychotropic Agents. II. Synthesis of 1-Substituted-3-(p-fluorophenacyl) piperidines and the Related Compounds

Abstract

A series of 1-substituted-3-phenacylpiperidine derivatives (VI) and 1-substituted-3-(p-fluorophenacyl) pyrrolidine derivatives (XI) were synthesized for pharmacological testing. The conversion of 3-phenacyl-4-piperidone derivatives (XXII) into 4, 5, 6, 7-tetrahydrofuro (or-1H-pyrrolo) [3, 2-c] pyridine derivatives (XX, XXV), the rearrangement of the quaternary salts of these products (XXa, XXVb) with phenyllithium and the dimerization of the dehydration product of 1-benzyl-3-hydroxymethyl-4-piperidone (K) were also described. Among the compounds synthesized, 1-(p-fluorobenzoyl) propyl-3-(p-fluorophenacyl)-pyrrolidine (XId) showed remarkable central nervous system depressing activities.