N-Alkylation of Amines and Amides Catalyzed by Ammonium Halides

Abstract

A new method was found for N-alkylation of amines and amides with alcohols in homogeneous liquid-phase. Addition of small amounts of ammonium halide to the reactants attained successfully high yields of N-alkyl or N, N-dialkyl derivatives of starting amines and amides at 280-320°C in the atmosphere of nitrogen. This N-alkylation reaction gave N, N-dialkylaniline from aniline, N-alkyl-α-pyrrolidone from α-pyrrolidone, N-alkyl-α-piperidone from α-piperidone, N, N-dialkylformamide from formamide (starting material : ammonium formate), and N, N-dialkylacetamide from acetamide (starting material : ammonium acetate).