Benzene, 1-(chloromethyl)-2-fluoro- → 1-Benzyl-4-(2-fluorobenzyl)piperidin-4-ol

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Reaction Steps

A suspension of Mg (3.50 g, 144 mmol) in diethyl ether (75 mL) was treated with 2-fluorobenzyl chloride (19.0 g, 131 mmol), stirred until all the Mg dissolved, treated with N-benzyl 4-piperidone (27.2 g, 144 mmol) in RATIO THF/diethyl ether (40 mL), and stirred at room temperature until the reaction was complete by TLC analysis. The mixture was partitioned between ethyl acetate and saturated NH4Cl and the aqueous layer was extracted with ethyl acetate twice. The combined organic layers were dried (MgSO4), filtered, and concentrated to give a residue which was used without further purification. MS (ESI) m/e 300 (M+H)+.

Provenance & Evidence