Pyridine → HCID 56617074, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 16.8 g. (50 mmole) ethyl 4-[2-(piperazin-1-yl)-ethyl]-benzoate dihydrochloride and 200 ml. anhydrous pyridine is added dropwise at 5°-10° C., in the course of 40 minutes, a solution of 14.8 g. 3,5-di-tert.-butyl-4-hydroxycinnamoyl chloride and 50 ml. anhydrous benzene. The reaction mixture is stirred for 4 hours at 20° C., the benzene and pyridine are substantially distilled off in a vacuum and the residue is stirred into about 1 liter ice water. The separated, greasy precipitate is taken up in methylene chloride and the methylene chloride phase is washed with aqueous sodium carbonate solution, dried with anhydrous sodium sulphate and evaporated to dryness in a vacuum. The crude base is dissolved in ethanol, gassed with hydrogen chloride and finally precipitated as the hydrochloride by the addition of diethyl ether. The yield is 17.3 g. (62% of theory) of the desired product which, after stirring up with diethyl ether, melts at 193°-195° C. (decomp.).

Provenance & Evidence