GB458511A - Improvements in the manufacture and production of amines and amides - Google Patents

Abstract

Amines and amides of the formula RN(CH3)2, in which R is any hydrocarbon or heterocyclic radicle or substitution product thereof, or any carboxylic acid radicle, are obtained by reacting compounds of the formula RX, where X is halogen linked directly to carbon, with an excess of dimethylamine under pressure with the practical exclusion of water and under such conditions that the dimethylamine hydrohalide formed as a by-product is permitted to settle out as a layer or precipitate at a temperature above 50 DEG C. The layer or precipitate of dimethylamine hydrohalide is then separated from the solution of the desired product in excess of dimethylamine, either directly or after the mixture has been cooled. The process is based on the observation that the hydrohalides of dimethylamine are practically insoluble in liquid anhydrous dimethylamine at temperatures above 50 DEG C. If the reaction is effected at above 100 DEG C., the hydrohalide is deposited as an oily layer; this may be separated immediately, or alternatively the mixture may be cooled (to below 50 DEG C. if desired) to convert the oily layer into a crystalline precipitate, which is then filtered; a crystalline precipitate is also obtained if a chlorine compound is used in the reaction and the latter is effected at 50--100 DEG C. Examples are given in which dimethylamine is reacted, under conditions as defined above, with (1) o-chloronitrobenzene, (2) benzyl chloride, (3) ethylene bromide, (4) butyl chloride, (5) ethylene chloride, (6) stearic acid chloride, (7) cyclohexyl chloride, and (8) 2-chloropyridine. Other halogen compounds which may be treated are ethyl chloride, bromide and iodide, dodecyl chloride, monochlorodecahydronaphthalenes, other chloronitrobenzenes, 2-chloroquinoline, acetyl chloride and benzoyl chloride.