1-(1-Naphthyl)piperazine → 4-{4-[2-(4-Naphthalen-1-yl-piperazin-1-yl)-ethyl]-phenyl}-thiazol-2-ol

Participants

Reaction Steps

To a 35 ml round-bottomed flask equipped with condenser and N2 inlet were added 1.40 g (5.84 mmol) of 4-(4-(2-chloroethyl)phenyl)thiazol-2-one, 1.24 g (5.84 mmol) of N-(1-naphthyl)piperazine, 0.81 ml (5.84 mmol) of triethylamine, 0.62 g (5.84 mmol) of sodium carbonate, 2 mg of sodium iodide, and 12 ml of methylisobutylketone. The reaction was heated at reflux for 5 days, cooled, and evaporated. The residue was taken up in ethyl acetate/water, the layers separated, and the ethyl acetate layer washed with brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using ethyl acetate/methylene chloride as eluent. The product fractions were evaporated, and the residue taken up in hot methylene chloride/methanol, treated with ethyl acetate saturated with hydrochloride, precipitated with ether, filtered, washed with ether, and dried to give 0.523 g (18%) of a white solid, m.p. 307°-309° C.

Provenance & Evidence