Boron tribromide → 2-(4-Benzyl-piperidin-1-yl)-N-(4-hydroxy-phenyl)-acetamide

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Reaction Steps

To a stirred solution of 0.68 g (2 mmol) of 2-(4-benzyl-piperidin-1-yl)-N-(4-methoxy-phenyl)-acetamide (Example 190) and in 30 ml of dichloromethane 0.95 ml (10 mmol) of boron tribromide in 9 ml of dichloromethane is added dropwise at −20° C., and the reaction mixture is stirred at room temperature for 10 hours. The reaction mixture is concentrated. Then 30 ml of 8% sodium hydrogenecarbonate solution and 20 ml of chloroform are added to the mixture. The organic layer is separated and the water phase is extracted three times with 20 ml of chloroform. The combined organic layers are dried over sodium sulfate, concentrated and the residue is purified by column chromatography using Kieselgel 60 as adsorbent (Merck) and chloroform:methanol=9:1 as eluent to yield 0.4 g (62%) of the title compound. Melting Point: 66-70° C. (hexane)

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