Potassium Iodide → N-(2-(1-naphthyl)ethyl)-4-(2-bromo-5-methoxybenzyl)piperidine

Beteiligte Stoffe

Reaktionsschritte

Methanesulfonyl chloride (100 μl, 1.26 mmol) was added dropwise to a solution of 1-naphthylethanol (206 mg, 1.20 mmol) and triethylamine (350 μl, 2.40 mmol) in dichloromethane (2 ml) under ice-cooling and stirred for 3 hours. The solvent was distilled off and the resulting residue was dissolved in acetonitrile (3 ml) together with a base converted from 4-(2-bromo-5-methoxybenzyl)piperidine hydrochloride (384 mg, 1.20 mmol) according to the method described in Example 11, potassium iodide (199 mg, 1.20 mmol) and potassium carbonate (332 mg, 2.40 mmol). The resulting solution was heated under reflux for 3.5 hours and then allowed to cool. The precipitate was filtered off and the filtrate was concentrated, and then the residue was purified by a silica gel column chromatography (chloroform:methanol=20:1) to obtain the title compound (425 mg, 81%) as a light-brown solid.

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