1-Butanol → 4-[Bis(4-fluorophenyl)methyl]-1-[3-(3,4-dimethoxyphenoxy)propyl]piperidine oxalate

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Reaction Steps

A mixture of 6.02 g (0.021 mole) of 4-[bis(4-fluorophenyl)-methyl]piperidine, 4.83 g (0.021 mole) of 4-(3-chloropropoxy)-1,2-dimethoxybenzene, and potassium carbonate (5.52 g, 0.04 mole) was heated at reflux overnight in 300 ml of 1-butanol containing potassium iodide (0.3 g). The reaction mixture was concentrated to dryness and partitioned between chloroform and water several times. The chloroform layer was dried over anhydrous sodium sulfate and then filtered. The chloroform was removed by rotary evaporator. The oil obtained was converted to the oxalate salt and then recrystallized from ethanol-ethyl ether and methanol isopropyl ether. This furnished 7.77 g (64.7%) of white solid, m.p. 188° C.

Provenance & Evidence