Alkylation of N-substituted 2-phenylacetamides: Benzylation of N-(4-nitrophenyl)-2-phenylacetamide

Abstract

N-(4-Nitrophenyl)-2-phenylacetamide was alkylated with benzyl chloride in the presence of powdered potassium hydroxide at different temperatures and in various solvents in order to establish the reactivity and orientation in the reaction. The reactions were also carried out in the presence of different phase-transfer catalysts in toluene. Product formation was followed by GC. The obtained results were compared to the results of the benzylation of other N-substituted 2-phenylacetamides, especially of N-phenyl-2-phenylacetamide.

Keywords

• alkylation
• benzylation
• 2-phenylacetamides
• phase-transfer catalysis.