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4-(4-Fluorophenyl)-1,2,3,6-tetrahydro-1-(phenylmethyl)pyridine (60 g, 225 mmol) was used as a raw material and dissolved in methanol (500 mL). To this solution, palladium/carbon hydroxide (20%, 5 g) was added and the reaction was shaken under hydrogen atmosphere (50 psi) for 48 hours. Upon completion of the reaction, the mixture was filtered through a glass fiber mat and washed with methanol. The filtrate was concentrated under reduced pressure to remove the solvent. The residue was dissolved in ethyl acetate and a 1 M solution of ether hydrogen chloride (300 mL) was added. The resulting solid was collected and recrystallized from 2-propanol to give 4-(4-fluorophenyl)piperidine hydrochloride as a colorless solid (30.5 g, 63% yield). Mass spectral data: m/z (ES+) 180 (M+1). The resulting 4-(4-fluorophenyl)piperidine hydrochloride sample (1 g, 4.64 mmol) was suspended in ethyl acetate and washed with saturated aqueous sodium carbonate. The organic layer was dried with anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure to give the title compound 4-(4-fluorophenyl)piperidine as a colorless oil (825 mg, 99% yield). Mass spectral data: m/z (ES+) 180 (M+1).

[1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 495 - 500
[2] Patent: US6218390, 2001, B1
[3] European Journal of Medicinal Chemistry, 2005, vol. 40, # 12, p. 1197 - 1205
[4] Patent: US2003/236250, 2003, A1. Location in patent: Page 19