United States Patent Office Patented Sept
3,274,211 United States Patent Office Patented Sept. 20, 1966 2 cording to the process of this invention. Other ketones 3,274,211 N-ALKYLATION OF AMDES AND MEDES which may be utilized to give particular N-alkylation Louis Schmerling, Riverside, III., assignor to Universal products include methyl ethyl ketone, methyl propyl Oil Products Company, Des Plaines, Ill., a corporation ketone, methylbutyl ketone, methyl amyl ketone, methyl of Delaware hexyl ketone, methyl heptyl ketone, methyl octyl ketone, No Drawing. Filed Feb. 4, 1964, Ser. No. 342,549 etc., ethyl ethyl ketone, ethyl propyl ketone, ethyl butyl 9 Claims. (Cl. 260-326) ketone, ethyl amyl ketone, ethylhexyl ketone, ethyl hep tyl ketone, etc., propyl propyl ketone, propylbutyl ketone, This invention relates to a novel process for the N propyl amyl ketone, propylhexyl ketone, etc., butylbutyl alkylation of carboxylic acid amides and imides. More ketone, butyl amyl ketone, butyl hexyl ketone, etc. particularly, this invention relates to the reductive alkyla Other suitable but not necessarily equivalent ketones com tion of carboxylic acid amides and imides to give N prise cyclic ketones including cyclohexanone, benzophe alkylation products. none, etc., alkyl aryl ketones, alkyl cyclohexyl ketones, The alkylation products herein contemplated are par aryl aryl ketones, aryl cyclohexyl ketones, etc., including ticularly adapted to the preparation of primary amines. 15 compounds like acetophenone, ethyl phenylketone, propyl For example, N-isobutylacetamide, the reductive alkyla phenyl ketone, butyl phenyl ketone, amyl phenyl ketone, tion product of acetamide and isobutyraldehyde, is hydro etc., methyl cyclohexyl ketone, ethyl cyclohexyl ketone, lyzed to isobutylamine and acetic acid, the latter being propyl cyclohexyl ketone, butyl cyclohexyl ketone, etc.
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