GB923855A - ª -halogenated amines and process for their manufacture - Google Patents

Abstract

a -Halogenated amines of formula <FORM:0923855/IV(a)/1> in which R1 and R2 each represent an alkyl or phenylalkyl radical or together with the nitrogen atom form the residue of a saturated heterocyclic ring system, X represents hydrogen or an aliphatic or aromatic hydrocarbon radical and Hal represents a halogen atom which in the case of fluorine may be bound in complex form are prepared by reacting a compound of formula <FORM:0923855/IV(a)/2> wherein Y represents wherein R3 and R4 have the meanings given for R1 and R2 and R5 is an aliphatic or aromatic hydrocarbon radical in the presence of an inert solvent and in the absence fo moisture, with an acid halide of formula R.CO.Hal in which R represents an unsubstituted or substituted aliphatic or aromatic radical which may be bound to the carbonyl group through a hetero atom (as in chloroformic ester). When using an acid fluoride its activity is preferably enhanced by adding a compound capable of binding the fluorine atom in a complex form, e.g. boron trifluoride. An inert gas may be present. Examples describe the preparation of: (1) N-chloromethyldiethylamine; (2) N-chloromethyldi-n-butylamine; (3) N-chloromethylpiperidine; (4) N-(a -chlorobenzyl)piperidine; (5) N-(a -chlorobenzyl)dimethylamine; (6) N-(a -bromoisobutyl)morpholine; (7) N-bromomethyldi-n-propylamine; (8) N-iodomethyl-piperidine; (9) N-(a -iodobenzyl)dimethylamine; (10) morpholino - N - methyl-tetrafluoroborate; (11) piperidino-N-methyl-tetrafluoroborate; (12) N-bromomethylbenzylmethylamine.