[Synthesis]
General procedure for the synthesis of (1-phenyl-4-piperidinyl)methanol from ethyl 1-phenylpiperidine-4-carboxylate: To a solution of ethyl 1-phenylpiperidine-4-carboxylate (2.6 g, 6.86 mmol) in tetrahydrofuran (THF, 32 mL) was slowly added lithium aluminum hydride (325 mg, 8.58 mmol) at 0 °C. The reaction mixture was kept stirred at 0 °C for 2 hours. Upon completion of the reaction, the reaction was quenched by careful addition of saturated aqueous ammonium chloride solution and the insoluble material was removed by decantation. The organic layer was separated and dried with anhydrous magnesium sulfate and subsequently concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1) to afford (1-phenyl-4-piperidinyl)methanol (1.3 g, 99% yield) as a colorless solid.1H NMR (400 MHz, CDCl3) δ (ppm): 1.25-1.46 (m, 3H), 1.62-1.69 (m, 1H), 1.83- 1.88 (m, 2H), 2.72 (td, J=12.2,2.4Hz, 1H), 3.55 (t, J=5.8Hz, 2H), 3.69-3.74 (m, 2H), 6.81-6.96 (m, 3H), 7.23-7.28 (m, 2H). |