GB805575A - Substituted amides of trihaloacetic acids - Google Patents

Abstract

The invention comprises compounds of the formula C(R)3.CO.N(R1).A.B. (wherein R is halogen, R1 is hydrogen or an alkyl, 3:4-dimethoxybenzyl or benzyl radical, A is a divalent saturated aliphatic hydrocarbon radical of two to six carbon atoms and B is a piperidino, morpholino, 2:6-dimethylmorpholino, pyrrolidino, pipecolino or dialkylamino radical) and their non-toxic acid addition salts. They may be prepared by reacting a trihaloacetic acid halide, ester or azide with the appropriate amino-alkyl-tertiary-amine or by reacting the metallated amide of a trihaloacetic acid with the appropriate tertiary amino-alkyl halide. Salt-forming acids referred to are hydrohalic, sulphuric, phosphoric, maleic, acetic, citric, oxalic, succinic, benzoic, tartaric, fumaric, mandelic, malic and ascorbic acids and 8-chlorotheophylline. In examples: (1) to (5) N-(b -morpholino-ethyl)-trichloracetamide hydrochloride and the corresponding piperidino and dimethylamino compounds, N - methyl - N - (b - dimethylaminoethyl)- and N-(3-pyrrolidinopropyl) - trichloracetamide hydrochlorides are prepared by admixture of trichloracetyl chloride and the appropriate amine in benzene and the preparation of the free base corresponding to the first of these compounds is referred to; (6) N-(b -piperidinoethyl) - tribromoacetamide hydrobromide is similarly prepared from tribromoacetyl bromide and N-(b -aminoethyl)-piperidine; (7) trifluoroacetyl chloride replaces the tribromoacetyl bromide of (6), the product being N-(b -piperidinoethyl)-trifluoroacetamide hydrochloride; (8) N - (3 - morpholinopropyl) - trichloracetamide hydrochloride is prepared by the method of (1) and liberation of the corresponding free base is referred to; (9) N-(b -aminoethyl)-morpholine and veratraldehyde in benzene give 1-morpholino - 2 - (31 : 41 - dimethoxybenzylidene - imino)-ethane, this is catalytically hydrogenated to give 1 - morpholino - 2 - (31:41 - dimethoxybenzylamino) - ethane (hydrochloride also described) and this with trichloracetyl chloride in acetone gives N - (b - morpholinoethyl) - N - (3:4 - dimethoxybenzyl) - trichloracetamide hydrochloride; (10) N - (b - morpholinoethyl) - N - benzyl - trichloracetamide hydrochloride is similarly prepared; (11) N-[b -(2:6-dimethylmorpholino)ethyl]- an N-[b -(alpha-pipecolino)ethyl]-trichloracetamide hydrochlorides are prepared by the method of (1).