Stereochemistry of 3-Methyl-4-phenylpiperidines Derived from Corresponding 4-Phenyl-4-piperidinols

Abstract

Catalytic reduction of 3- and 5-methyl-4-phenyl-1,2,5,6-tetrahydropyridines is stereospecific and gives cis-3-methyl-4-phenylpiperidines. Hydrogenolysis of 1-t-3-dimethyl-4-r-hydroxy-4-phenylpiperidine (β-prodinol) by Raney nickel also gives a cis product. Stereochemical assignments are made on the basis of p.m.r. spectroscopic data. Hot-plate activities in mice of 1-methyl- and 1-phenethyl-c-3-methyl-4-phenylpiperidine are reported.