Sodium hydride → 4-(4-Bromophenylmethyl)-1-(1-(4-pyridyl)piperidin-4-ylcarbonyl)piperazine

1-(1-(4-Pyridyl)piperidin-4ylcarbonyl)piperazine (0.722 g) was dissolved in dry dimethylformamide (22 mL) and treated with sodium hydride (0.19 g, 45-55% dispersion, 4 mmol) under argon atmosphere. The resultant mixture was then allowed to stir for 30 minutes before the addition of 4-bromobenzyl bromide (0.66 g). The reaction was then stirred at room temperature for 2 hours and then quenched by pouring into water, basifying with saturated aq.NaHCO3 and then extracting with diethyl ether. The combined organic extracts were then washed with water, brine, dried (MgSO4) and then evaporated to afford a crude, cream solid which was then recrystallised twice from ethyl acetate/isohexane to give 4-(4-bromophenylmethyl)-1-(1-(4-pyridyl)piperidin-4-ylcarbonyl)piperazine as a white solid; m.p. 148-149° C.;