Sodium Hydroxide → 1-Benzyl-4-(pyridin-2-yl)piperidine-4-carbonitrile

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Combine 2-pyridylacetonitrile (5.9 g, 50 mmol), N-benzyl-N,N-bis-(2-chloroethyl)amine hydrochloride (13.4 g, 50 mmol), and hexadecyltributyphosphonium bromide (1.3 g, 2.5 mmol) and a 50% aqueous sodium hydroxide solution (75 mL). Heat to 100° C. After 1 hour, cool the reaction mixture to ambient temperature and repeatedly extract with diethyl ether. Extract the combined organic layers twice with an aqueous 10% hydrochloric acid solution (350 mL). combine the aqueous layers and neutralize with an aqueous 50% sodium hydroxide solution. Again extract three times with diethyl ether, combine the organic layers, dry over MgSO4, filter, and evaporate in vacuo to give 1-benzyl-4-cyano-4-(pyridin-2-yl)-piperidine: Rf =0.56 (silica gel, 9/1 dichloromethane/methanol). Elemental Analysis calculated for C18 H19N3 : C, 77.95; H, 6.90; N, 15.15. Found: C, 78.20; H, 6.97; N, 15.04.

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