GB808636A - Basically substituted heterocyclic compounds - Google Patents

Abstract

The invention comprises compounds of the formula <FORM:0808636/IV (b)/1> and salts thereof, wherein R is a benzene ring and <FORM:0808636/IV (b)/2> is the residue of a tertiary amine, which may optionally bear substituents which do not react with halogenoalkyl compounds, such as alkyl alkoxy and aryloxy radicals and the corresponding thio radicals, in the 4-position and/or in the residue R. The compounds are made by reacting the corresponding 1 - oxo - 1 : 2 - dihydrophthalazine, suitably in the form of its alkalimetal salt, with a teritary aminoalkyl halide preferably at 40-60 DEG C. Suitable tertiary aminoalkyl halides include the diethylamino-, dibutylamino-, piperidino-, morpholino- and N-methylanilino-, ethyl chlorides and 1-dimethylamino - 2 - chloropropane and 2 - dimethylamino - 5 - chloropentane. The products are suitable isolated in the form of their acid addition salts such as the hydrochlorides, hydrobromides, sulphates, picrates, benzoates, salicylates and gentisates. Examples describe the preparation of 2-(b -diethylaminoethyl), 2-(b -dimethylaminoethyl), 2 - (a - methyl - b - dimethylaminoethyl), 2 - (b - piperidinoethyl) and 2 - (b - dibutylaminoethyl), 1 - oxo - 1 : 2 - dihydrophthalazine and also the 2-(b -diethylaminoethyl), 4 - methyl -, 4 - methoxy -, 4ethylthio -, and 4 - b - diethylaminoethoxy-, 1-oxo-1 : 2-dihydrophthalazines. 4 - Substituted - phthalazines. The 4 - b - diethylaminoethoxy -, 4 - methoxy - and 4 - ethylthio - 1 - oxo - 1 : 2 - dihydrophthalazines used as starting materials are prepared by treating 1 : 4-dichlorophthalazine with sodium diethylaminoethoxide, sodium methoxide and sodium ethylmercaptide respectively to replace one halogen atom and replacing the second halogen atom by hydrolysis.