GB833008A - Improvements in and relating to diquaternary compounds - Google Patents

Abstract

The invention comprises compounds of the general formula <FORM:0833008/IV (b)/1> in which R1 is a C1-4 alkyl, or alkoxy group, a phenyl or a hydroxy group; R2 is a methyl or an ethyl group; n is an integer from 2 to 6; N +1 and N +2 are quaternary atoms each carrying two alkyl groups which are methyl or ethyl groups or either N +1 or N +2 may be part of a pyrrolidine, morpholine or piperidine ring; Y is an alkylene chain having two to four carbon atoms and A-is an anion of an inorganic or organic acid. The compounds of the invention may be prepared by treating a diamine <FORM:0833008/IV (b)/2> (N3 being a secondary or tertiary nitrogen atom and N4 a primary, secondary, tertiary or quaternary nitrogen atom or else N3 is a quaternary nitrogen atom and N4 is a primary, secondary or tertiary nitrogen atom) with a quaternizing agent. Both the Provisional Specifications relate to compounds of the general formula <FORM:0833008/IV (b)/3> wherein R1 and R2 are phenyl groups, optionally substituted by halogen atoms or alkyl groups (the total number of carbon atoms therein not exceeding three); R3 is a C1-4 alkyl anhydroxy or a phenyl group, m is 2-6; N +1 is a quaternary nitrogen atom either carrying two alkyl groups or forming part of a pyrrolidine, morpholine or piperidine ring; N +2 is similar but carries at least one methyl or ethyl group in addition; Y and A having the meaning above. In the second Provisional Specification the group N +1.Y.N +2 may represent a piperazine ring in which N +1 is a quaternary nitrogen atom carrying one methyl or ethyl group and N +2 a quaternary nitrogen atom carrying two alkyl groups. Diamines of the formula (II) (where N3 is a secondary or tertiary nitrogen atom and N4 is a tertiary nitrogen atom, R1 an alkyl, phenyl or alkoxy group and n is 3-6) are prepared by reacting a compound of the general formula R1COCH(C6H5)2 (III) with a polymethene a : o -dihalide of the formula X-(CH2)n-Z (IV) (where X and Z are different halogen atoms) to give a compound of the general formula R1COC(C6H5)2(CH2)nZ (V) and reacting this with a diamine N5-Y-N4 (VI) (where N5 is a primary or secondary nitrogen atom). Diamines of formula (II) (where R1 is a hydroxy group) are prepared by hydrolysis of (II), where R1 is alkoxy or of compounds of the general formula <FORM:0833008/IV (b)/4> and (where R1 is an alkyl or a phenyl group and n is two) the compound (VII) is reacted with a suitable organometallic compound such as an alkyl or phenyl Grignard reagent. The corresponding starting materials of the Provisional Specification are similarly prepared. Specification 787,279 is referred to.