1-Butanol → N,alpha-Bis(4-Fluorophenyl)-1-[2(2-naphthalenyloxy)ethyl]-4-piperidinemethanamine hydrochloride

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A mixture of N,α-bis(4-fluorophenyl)-4-piperidinemethanamine (3.42 g, 0.0113 mol), 2-bromoethyl naphthyl ether (2.83 g, 0.0113 mol), and potassium carbonate (3.46 g, 0.025 mol) was heated at reflux 16 h in 350 mL of 1-butanol containing sodium iodide (0.2 g). The reaction was concentrated to dryness, and the residue partitioned between chloroform and water. The chloroform layer was extracted with 5% sodium hydroxide. The organic layer was dried (Na2SO4) and filtered. The chloroform was removed by rotary evaporator to give a brown residue. This material was subjected to flash chromatography on silica gel. Elution was accomplished using methylene chloride, 1% methanol-methylene chloride, and 2% methanol-methylene chloride. Fractions of similar purity were combined and solvents removed. A brown residue was obtained and converted to the HCl salt in methanol-diethyl ether and placed in the freezer. A white solid was isolated and dried 16 h at 78° C. This process provided 2.24 g (36.3%) of white crystalline product mp 226°-230° C. (dec.).

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