Diphenylpiperidines: Synthesis and properties of some methoxy-substituted 3,4-diphenylpiperidine derivatives

Abstract

The α- and β-racemates of a series of methoxy-substituted N-ethyl-3,4- diphenylpiperidines have been synthesized by reductive cyclization of the appropriately substituted ethyl 3,4-diphenyl-4-cyanobutanoates prepared by Michael condensation of the corresponding phenylacetonitriles with ethyl cinnamate derivatives. The mechanism of the reduction, the stereochemistry, and the N.M.R. spectra of the racemates are discussed.