Patent GB-934630-A (GB)
Title: N-heterocyclic compounds and process for the production thereof
IPC: C07D401/06
Filed: 1959-12-04
Abstract: The invention comprises compounds of the general formula <FORM:0934630/IV(a)/1> (wherein X represents -CH2-CH2- or -CH=CH-, R represents a C2-4 alkyl radical or a chlorine or bromine atom, Y represents a C2-6 alkylene radical with 2-4 carbon atoms in the direct chain between N and Am, and Am represents a di-(C1-4 alkyl)-amino group wherein one of the alkyl radicals may be bound direct to Y or the two alkyl radicals may be bound together direct or through an oxygen atom or an alkylimino, hydroxyalkylimino or alkanoyloxyalkylimino group, but excluding compounds in which X is -CH2-CH2-, R is C2-4 alkyl and the two alkyl groups in Am are bound together through an alkylimino group and compounds in which X is -CH2-CH2-and Am is a hexamethyleneimino radical which may be substituted by one or more C1-3 alkyl groups), and their acid addition and quaternary ammonium salts, and the preparation thereof by (a) reacting a compound of the general formula <FORM:0934630/IV(a)/2> with a reactive ester of an aminoalcohol of the general formula HO-Y-Am III in the presence of a condensing agent, or (b) heating a compound of the general formula <FORM:0934630/IV(a)/3> until one molecular proportion of carbon dioxide is split off, or (c) reacting a reactive ester of a compound of the general formula <FORM:0934630/IV(a)/4> with a secondary amine of the general formula Am-H VI (wherein an alkyl group of Am cannot be linked to Y), or (d) alkylating a corresponding compound in which Am is NH2 or a monoalkylamino group, or (e) reducing a compound of the general formula <FORM:0934630/IV(a)/5> p  (wherein Y1 and Am2 have the meanings given for Y and Am except that at least one CH2 group attached to a nitrogen atom is replaced by CO) by means of an alkali metal-earth metal hydride, and in all cases, if desired, converting the product into a salt by reaction with an inorganic or organic acid or into a quaternary ammonium compound by addition of a reactive ester of an aliphatic or araliphatic alcohol.  Compounds of the general formula IV are prepared by reacting compounds II with phosgene and then reacting the products with compounds III.  Reactive esters of compounds of the general formula V are prepared by reacting the compounds with inorganic acid halides or alkyl or aryl sulphonyl chlorides.  Amino- and monoalkylamino-compounds used in process (d) are prepared by a process similar to (c) or by reduction of the corresponding cyano-alkyl compounds.  Compounds of the general formula VIII are prepared by reaction of alkali metal compounds of the appropriate 3-R-iminodi-benzyls or -iminostilbenes with a -bromoalkane carboxylic acid dialkylamides, piperidides morpholides or -4-alkyl-piperazides or with halogen alkane carboxylic acid halides and their amines of formula VI; or by reacting reactive esters of compounds of formula V with alkali metal compounds of alkane carboxylic acid-N-alkylamides, succinimide or glutarimide or by acylating the starting materials used in process (d).  3-Chloro-5- (Y-chloropropyl)-iminodibenzyl is prepared from 3-chloro-iminodibenzyl and 1-chloro-3-bromo-propane.  Specifications 912,013 and 914,717 are referred to.