GB770625A - Substituted endoxy-perhydrophthalimides - Google Patents

Abstract

The invention comprises substituted endoxyperhydrophthalimides of the general formula <FORM:0770625/IV(b)/1> wherein the <FORM:0770625/IV(b)/2> ring may contain alkyl substituents, R represents an alkyl group containing from 1 to 6 carbon atoms or <FORM:0770625/IV(b)/3> represents the residue of a saturated nitrogencontaining heterocyclic base, and x is a whole number from 2 to 6, and the acid addition and quaternary salts thereof, and of the general formula <FORM:0770625/IV(b)/4> wherein the <FORM:0770625/IV(b)/5> ring may contain alkyl substituents and R1 represents a straight chain alkyl radical or a branched chain alkyl radical containing one branched chain and having 1 to 12 carbon atoms, and the preparation of compounds of both general formul by reacting the required dialkylamino-, heterocyclic-alkyl- or alkyl-amine with the desired acid anhydride (preferably in equimolecular quantities) to form an acid amide which is cyclized to the desired imide by heating, and, if desired, the compounds of the first general formula are converted into acid addition and quaternary salts thereof. The group <FORM:0770625/IV(b)/6> may represent the residue of piperidine, morpholine or pyrrolidine, and R1 may represent a methyl, isopropyl or isoamyl radical. The alkyl ring substituted compounds of the above perhydrophthalimides may contain 3-methyl-, 3,6-dimethyl-, 1,2-dimethyl-, or 3,4,5,6-tetramethyl-substituents. The cyclization step may be brought about by heating for 2 to 5 hours, a suitable temperature being in the range of 160 DEG to 180 DEG C. In the examples the following compounds are prepared: N-b -dimethylaminoethylperhydro - 4,7 - endoxyperhydrophthalimide and the hydrochloride salt thereof, and N - b - diethylaminoethyl -, N - g - dimethylaminopropyl-, N - g - diethylaminopropyl-, N - g - dibutylaminopropyl -, N - b - dihexylaminoethyl-, N - o - diethylaminohexyl-, b - (N-morpholino) ethyl-, g - (N - morpholino) propyland b - (N - piperidino) ethyl - perhydro - 4,7 - endoxyperhydrophthalimides, N - b - dimethylaminoethyl - 3,6 - dimethyl - 3,6 - endoxyperhydrophthalimide and the hydrochloride salt thereof, N - b - dimethylaminoethyl - 3 - methyl-3,6 - endoxyperhydrophthalimide and the hydrochloride salt thereof, N-b -dimethylaminoethyl - 1,2 - dimethyl - 3,6 - endoxyperhydrophthalimide and the hydrochloride salt thereof, and N - methyl - 3 - methyl - 3,6 - endoxyperhydrophthalimide. The quaternary salts may be derived from alkyl compounds to introduce alkyl groups which may or may not be the same as the R group, e.g. a methyl, ethyl, allyl or decyl group may be introduced.