General procedure for the synthesis of 4-(4-bromophenyl)piperidine from 4-(4-bromophenyl)-1,2,3,6-tetrahydropyridine: to a solution of 4-(4-bromophenyl)-1,2,3,6-tetrahydropyridine (0.90 g, 3.78 mmol) in anhydrous methanol (20 mL) and triethylamine (2 mL), the Rh/C catalyst (0.060 g, J. Bishop & Co. Platinum). The reaction mixture was placed in a hydrogen atmosphere (100 psi) and stirred at room temperature for 24 hours. Upon completion of the reaction, the mixture was filtered through a Celite?(Sigma Aldrich, St. Louis, MO) filter cake and the filtrate was concentrated to afford 4-(4-bromophenyl)piperidine as a white solid (0.91 g, 98% yield). The product was confirmed by 1H NMR (400 MHz, MeOD): δ 1.55-1.59 (2H, m), 1.61-1.70 (2H, m), 2.55-2.56 (1H, m), 2.64-2.70 (2H, m), 3.09-3.06 (2H, m), 7.13 (2H, J = 8.0 Hz, d), 7.31 ( 2H, J = 8.0 Hz, d).13C NMR (100 MHz, MeOD): δ 32.7, 41.4, 45.6, 119.4, 126.4, 128.2, 128.5, 131.2, 145.3. m/z of mass spectrum (ESI-MS): 241 [M+H]+.
