Water → Benzyl 4-(4-(chloromethyl)pyridin-2-yl)piperazine-1-carboxylate

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Reaction Steps

To a solution of benzyl 4-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-2-yl)piperazine-1-carboxylate (7.3 g, 17.7 mmol) in DCM (30 mL), thionyl chloride (7.7 mL, 106.6 mmol) was added slowly at RT, followed by the addition of H2O (0.05 mL). The mixture was stirred at RT overnight, poured into a solution of aqueous NaHCO3 (sat., 50 mL), and extracted with DCM (2×30 mL). The combined organic layers were washed with H2O (50 mL) and brine (20 mL), dried over Na2SO4, filtered, and concentrated to afford the crude product, which was purified by silica gel column chromatography (Petroleum ether:EtOAc=3:1) to give benzyl 4-(4-(chloromethyl)pyridin-2-yl)piperazine-1-carboxylate as a yellow solid (5.0 g, 82%). MS (ES+) C18H20ClN3O2 requires: 345, found: 346 [M+H]+.

Provenance & Evidence