GB807837A - New tertiary amines and their salts and process for their preparation - Google Patents

Abstract

The invention comprises tertiary amines of the general formula <FORM:0807837/IV (b)/1> and acid addition and quaternary salts thereof, in which R1 and R2 are each an alkyl or hydroxyalkyl group of 1-6 carbon atoms or a cycloalkyl, monocyclic aryl, or monocyclic aralkyl group or NR1R2 together forms a heterocyclic ring which may contain a further hetero-atom, for example a pyrrolidine, piperidine or morpholine ring, R3 is hydrogen or an hydroxyl or an alkyl or alkoxy group of 1-6 carbon atoms, R4 is hydrogen or together with R3 forms a methylene dioxy group, R5 is hydrogen or an alkyl or alkoxy group of 1-3 carbon atoms and Z is a straight or branched chain alkylene residue of 2-4 carbon atoms. The amines are prepared by condensing a tertiary aminonitrile of the formula <FORM:0807837/IV (b)/2> with an organo-magnesium halide of the formula Hal-Mg-Z-C6H4-R5 or, in the case where Z contains 2 or 3 carbon atoms, by condensing a nitrile of the formula <FORM:0807837/IV (b)/3> with an organo-magnesium halide of the formula <FORM:0807837/IV (b)/4> the reactions being carried out in an inert solvent such as ether, dioxan, benzene, dibutyl ether or a mixture of benzene and tetrahydrofuran, preferably at the boiling-point of the solvent, followed by hydrolytic decomposition of the initial condensation product. The amines may be converted into their acid addition salts such as the hydrochloride, hydrobromide, sulphate, phosphate, nitrate, acetate, propionate, butyrate, valerate, oxalate, malonate, succinate, maleate, fumarate, lactate, tartrate, citrate, malate, benzoate, phthalate, cinnamate, salicylate, nicotinate or furan-2-carboxylate, or into their quaternary salts with alkyl halides, dimethyl sulphate, diethyl sulphate, alkyl p-toluenesulphonates, cyclohexyl halides or cyclopentyl halides. Preferred products include the 1-(4-methoxyphenyl)-1-dimethylamino -, 1 - (4 - ethoxyphenyl) - 1 - dimethylamino -, 1 - (4 - ethoxyphenyl) - 1 - diethylamino -, 1 - (4 - methoxyphenyl) - 1 - pyrrolidino -, 1 - (4 - methylphenyl) - 1 - dimethylamino - and 1 - (4 - methylphenyl) - 1 - piperidino -, 3 - methyl - 3 - phenyl - propanes; the 1-(3:4 - methylenedioxyphenyl) - 1 - dimethylamino-, 1-(4-methylphenyl)-1-piperidino-, 1-(4-methylphenyl) - 1 - dimethylamino -, 1 - (4 - isopropylphenyl) - 2 - methyl - 3 - dimethylamino- and 1 - phenyl - 3 - dimethylamino -, 3 - phenyl - propanes; 1:4 - diphenyl - 1 - pyrrolidino - butane; 1 - phenyl - 1 - methyl - 2 - dimethylamino - 2 - (4 - methoxyphenyl) - ethane and 1 - phenyl - 3 - dimethylamino - 3 - (4 - methoxyphenyl) - propane. Many other examples are given. a - Tertiary amino nitriles of the formul II and III are made by known methods, for example by the reaction of the appropriate phenylalkyl aldehyde with potassium cyanide and a secondary amine of the formula NHR1R2.