Diastereoisomeric esters of 1,2-dimethyl-4-phenylpiperidin-4-ol and related compounds

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Abstract
The synthesis of 1,c-2- and 1,t-2-dimethyl-4-phenylpiperidin-r-4-ols and derived esters is reported. Configurations and preferred conformations are assigned on the basis of reactivity of the alcohols towards thionyl chloride and Raney nickel, 1H n.m.r. characteristics, and the observation of epimeric conjugate acids in cis-derivatives. The stereochemistry of the hydrogenolysis products is confirmed by comparing N-methyl chemical shifts of methiodide derivatives with those calculated from the shielding influence of 2eq- and 2ax-methyl substituents. The hot-plate ED50 values (for mice) of acetate and propionate esters of the piperidinols are reported and compared with those of analogues lacking 2-methyl substituents.

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