Hydrochloric Acid → 4-(4-(2-(4-(1-Naphthyl)piperazinyl)ethyl)phenyl)-2-aminothiazole

Participants

Reaction Steps

To a 35 ml round-bottomed flask equipped with condenser and N2 inlet were added 3.19 g (10 mmol) of 4-(4-(2-chloroethyl)phenyl)-2-aminothiazole hydrobromide, 2.12 g (10 mmol) of N-(1-naphthyl)piperazine, 2.79 ml (20 mmol) of triethylamine, 1.06 g (10 mmol) of sodium carbonate, 2 mg of sodium iodide, and 25 ml of ethanol. The reaction was heated at reflux for 5 days, cooled, and the precipitate filtered, and washed with ethanol and water. The orange solid was chromatographed on silica gel using ethyl acetate/methylene chloride as eluent to give a white solid. The solid was taken up in ethyl acetate/methanol, ether saturated with HCl added, the precipitate filtered, washed with ether, and dried to give a white solid, 1.61 g (31%), m.p. 274°-277° C.

Provenance & Evidence