HCID 46926628, compound → 4-(3-(4-(Hydroxydiphenylmethyl)piperidin-1-yl)propoxy)benzonitrile

Participants

Reaction Steps

4-(3-(4-Benzoylpiperidin-1-yl)propoxy)benzonitrile (0.5 g, 1.4 mmol) was dissolved in dry THF (˜15 mL), and a solution of phenylmagnesium bromide (0.9 mL, 2M, 1.8 mmol) was added and the reaction stirred for 6 h. The reaction was quenched (sat. NH4Cl) and extracted into EtOAc (2×). The organic layers were dried over Na2SO4 and the volatiles removed under reduced pressure. The crude residue was purified on silica gel (EtOAc/hexanes) to give 417 mg (70% yield) of title compound Example B1: 1H NMR (400 MHz, CDCl3) δ 7.58 (2H, d, J=8.8 Hz), 7.50 (4H, d, J=7.6), 7.30 (4H, q, J=8), 7.20 (2H, t, J=7.2 Hz), 6.94 (2H, d, J=8.8 Hz), 4.06 (2H, t, J=6 Hz), 3.07 (2H, d, J=11.2 Hz), 2.59 (2H, t, J=7.2 Hz), 2.53-2.46 (1H, m), 2.14-2.01 (4H, m), 1.66-1.55 (4H, m), LC-MS (>98%) m/z=427.0 [M+H]; HRMS=427.2386 [M+H], 100% calculated for C28H31N2O2, 427.2386.

Provenance & Evidence