Potassium Cyanide → Benzyl 4-(4-(cyanomethyl)pyridin-2-yl)piperazine-1-carboxylate

Participants

Reaction Steps

A solution of benzyl 4-(4-(chloromethyl)pyridin-2-yl)piperazine-1-carboxylate (5.0 g, 14.5 mmol) and KCN (2.8 g, 43.5 mmol) in DMSO (30 mL) was stirred at RT overnight, and then diluted with sat. NaHCO3 (300 mL) and extracted with EtOAc (3×200 mL). The combined organic layers were washed with H2O (50 mL) and brine (20 mL), dried over Na2SO4, filtered and concentrated to afford crude product, which was purified by silica gel column chromatography (Petroleum ether:EtOAc=1:1) to give benzyl 4-(4-(cyanomethyl)pyridin-2-yl)piperazine-1-carboxylate as a yellow solid (2.5 g, 51%). MS (ES+) C19H20N4O2 requires: 336, found: 337[M+H]+.

Provenance & Evidence