Hydrochloric Acid → N-(3,4-Difluorophenyl)-alpha-(4-fluorophenyl)-1-[2-(1-naphthalenyloxy)ethyl]-4-piperidinemethanamine dihydrochloride

Beteiligte Stoffe

Reaktionsschritte

A mixture of 4-[[(3,4-difluorophenyl)amino](4-fluorophenyl)methyl]piperidine (5.41 g, 0.0169 mol), 1-(2-bromoethoxy)naphthalene (4.23 g, 0.0169 mol) and sodium bicarbonate (5.53 g, 0.059 mol) in 350 mL of 1-butanol containing sodium iodide (0.2 g) was heated 20 h at reflux. The reaction was concentrated to dryness and partitioned between chloroform and water. The chloroform layer was washed with 5% sodium hydroxide and dried (Na2SO4). Chloroform was removed to give a brown oil. The oil was dissolved in methylene chloride and placed on a silica gel column for flash chromatography. Elution was accomplished using 1% methanol-methylene chloride and 2% methanol-methylene chloride. Fractions of similar purity were combined and solvents removed to give a fluffy grey material. This material was converted to the HCl salt and the salt was recrystallized from methanol-diethyl ether to give a whitish-grey solid. The material was dried 16 h in vacuo at 80° C. This process provided 5.06 g (53.1%) of greyish material, mp 212°-215° C. (dec).

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