1-Butanol → n-Butyl 3-[4-(piperazin-1-yl)-phenyl]-propionate

Participants

Reaction Steps

A mixture of 175 g. (0.79 mole) n-butyl 3-(-4-aminophenyl)-propionate (prepared by the hydrogenation of n-butyl 4-nitrocinnamate in the presence of palladiumcharcoal in n-butanol; b.p. 137°-138° C./0.013 mbar), 141.3 g. (0.79 mole) bis-(2-cholorethyl)-amine hydrochloride and 600 ml. n-butanol is maintained at reflux temperature for 48 hours, then 54.5 g. (0.39 mole) powdered potassium carbonate are added thereto and the reaction allowed to continue for a further 120 hours at the boiling temperature. Thereafter, the reaction mixture is suction filtered hot, the filtrate is evaporated in a vacuum and the oil remaining behind is taken up in n-butanol. The sulphate is now precipitated out in the cold by adding concentrated sulphuric acid. It is filtered off with suction, triturated with diethyl ether and dried. Yield 286.8 g. (69% of theory); m.p. 183°-185° C.

Provenance & Evidence