Reaction of Amide Homologs. XIII. Catalytic Hydrogenolysis of N-Acylaminomethyl and N-Arylsulfonamidomethyl Compounds

Abstract

Hydrogenolysis of N-acylaminomethyl and additionally N-arylsulfonamidomethyl compounds attached to a variety of amines, not only under conditions with Raney nickel catalyst under high hydrogen pressure, but also, in some cases, under those with palladium-on-charcoal catalyst under ordinary hydrogen pressure, was investigated in a view of the factors affecting the rate. Solvent and variation in the structure were recognized to be major rate-determining factors. Comparison of the rates of a large number of the compounds indicates that the hydrogenolysis is more facilitated with increase of electron density at amine nitrogen and decrease of that at each acylamino and sulfonamido nitrogen. The reaction scope was established and the application in N-methylation of amine was generalized.