GB711654A - Manufacture of new trialkylamines - Google Patents

Abstract

The invention comprises tris-(2-dialkylaminoethyl)-amines of the formula <FORM:0711654/IV (b)/1> where R-R5 are alkyl radicals of not more than 4 carbon atoms, i.e. methyl, ethyl, propyl or butyl, and their acid addition salts. The amines are prepared by treating the reactive ester of a corresponding dialkylamino ethanol of the formula (R)(R1).N.CH2.CH2.X where X is a reactive esterified hydroxyl group, especially a halogen atom, with ammonia or with an amine of the formula <FORM:0711654/IV (b)/2> or (R2)(R3).N.CH2.CH2.NH2. They may also be prepared by reacting an amine of the formula N(CH2.CH2.X)3 with an amine of the formula (R)(R1).NH. They may also be prepared by treating the corresponding acid amide wherein at least one of the ethylene radicals is replaced by a -CH2CO-group, with a reducing agent such as lithium aluminium hydride. They may also be prepared by treating an amine of the formula N(CH2.CH2.NY2)3 where one Y is hydrogen and the others are hydrogen atoms or lower alkyl radicals with an agent capable of introducing a lower alkyl radical such as an alkyl halide, or with formaldehyde in the presence of formic acid. In examples: (1) N : N-diethylethylene diamine is treated with 2-diethylaminoethyl chloride to give tris-(2-diethylaminoethyl)-amine which is converted to its trihydrochloride and tricitrate; (2) 2-di-n-butylaminoethyl chloride is treated with N : N-diethyl-ethylene diamine to give bis-(2-di-n-butylaminoethyl) - 2 - diethylaminoethylamine and its trihydrochloride; (3) tris-(2-chlorethyl)-amine is treated with di-isopropylamine to give tris-(2-di-isopropylaminoethyl)-amine tetrahydrochloride; (4) tris-(2-aminoethyl)-amine hydrochloride is heated with a mixture of formaldehyde and formic acid to give tris - (2 - dimethylaminoethyl) - amine tetrahydrochloride; (5) 2-dimethylaminoethyl chloride is treated with 2-dimethylaminoethylamine to give the product of (4); (6) tris-(2-chlorethyl)-amine hydrochloride is treated with dimethylamine to give the product of (4); (7) 2-dimethylaminoethyl chloride is reacted with anhydrous ammonia to give the product of (4) and (8) tris-(N : N-dimethyl-carbamylmethyl)-amine is reduced with lithium-aluminium hydride to give the product of (4). Tris - (2 - aminoethyl) - amine is obtained by hydrolysis of tris - (2 - phthalimidoethyl)-amine, or by reduction of tris-(cyano-methyl)-amine with hydrogen and Raney nickel or with lithium-aluminium hydride. Tris - (N : N - dimethyl - carbamylmethyl)-amine is obtained by treating tris-(chlorocarbonylmethyl)-amine with dimethylamine.