Benzylation of N-benzyl-2-phenylacetamide

Abstract

N-Benzyl-2-phenylacetamide was used as a model for the study of the alkylation of N-substituted 2-phenylacetamides with benzyl chloride in the presence of powdered KOH. The reactions were carried out in the presence and absence of phase-transfer catalysts, in order to establish any possible difference in the reaction products. Various phase-transfer catalysts, solvents and temperatures were used. A comparative study with the benzylation reaction of other N-substituted-2-phenylacetamides is presented. The observed lower reactivity of N-benzyl-2-phenylacetamide in comparison with the reactivity of N-ethyl-2-phenylacetamide and N-phenyl-2-phenylacetamide can be explained in terms of steric and polar effects.