4-amino-2-halobenzyl alcohols

摘要

1,136,483. 4 - Amino - 2 - halobenzyl alcohols. STERLING DRUG Inc. 18 March, 1966 [1 April, 1965], No. 12156/66. Heading C2C. Novel 4 - [amino - (polycarbon - lower - alkyl) - amino] - 2 - halobenzyl alcohols or their esters or acid-addition salts of the alcohols or esters are prepared by (a) reacting the corresponding 4 - [amino - (polycarbon - lower - alkyl) - aminol - 2 - halo - benzaldehyde or C 1-6 alkyl 4-[amino-(polycarbon-lower-alkyl)- amino - 2 - halobenzoate or C 1-6 alkyl 4-aminoacetylamino-2-halobenzoate with a reducing agent, or (b) subjecting a 4-[amino-polycarbonlower-alkyl)-amino-2-halotoluene to fermentative enzymatic oxidation by an organism classified in the orders Moniliales, Mucorales, Sphaeriaeles, Sphaeropsidales, Melanconiales and Actinomycetales and (c) if desired, esterifying the alcohol obtained to produce an ester, and/or, reacting a free base product to form a salt. The term " amino - (polycarbon - lower - alkyl) - amino " is defined as two amino groups which are connected by a C 2-6 alkylene chain optionally substituted by C 1-6 alkyl groups and having its connecting linkages on different carbon atoms, or in which the two amino groups form part of a piperazino group which may be N1- substituted. The novel compounds have schistosomacidal properties. 2 - Chloro - 4 - (4 - propionyl - 1 - piperazinyl) toluene and its p-toluenesulphonate are prepared by reacting 1 - (3 - chloro - 4 - methylphenyl)- piperazine with propionic anhydride and treating the product with p-toluene sulphonic acid monohydrate. Ethyl 2 - chloro - 4 - (2 - diethylamino - ethylamino)benzoate and its picrate are prepared by reacting ethyl 4-amino-2-chloro-benzoate and treating the product with picric acid. 1 - (4 - Carboethoxy - 3 - chlorophenyl) - piperazine and its hydrobromide and picrate are prepared by reacting ethyl 4 - amino - 2 - chlorobenzoate with bis-(2-bromoethyl)-amine hydrochloride to form the hydrobromide, basifying to form the free base and treating this with picric acid. Ethyl 2 - chloro - 4 - (diethylaminoacetamido) benzoate and its hydrochloride are prepared by reacting ethyl 4-amino-2-chloro-benzoate with chloroacetyl chloride to form ethyl 2-chloro-4- (chloro-acetamido)-benzoate, reacting this with diethylamine and treating the product with hydrochloric acid. 2 - Chloro-4-(2 - diethylamino-ethylamino)-3,5- dimethylbenzaldehyde is prepared by reacting 3- chloro-2,6 - dimethylaniline with 2-diethylaminoethyl chloride to form 3-(2 diethylaminoethylamino)-2,4 - dimethylclorobenzene and treating this with sodium 5-nitro-o-toluene sulphonate, ammonium chloride, zinc dust, hydrochloric acid and formaldehyde.