Benzyl chloroformate → Benzyl 4-(aminomethyl)piperidine-1-carboxylate--hydrogen chloride (1/1)

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Reaction Steps

To a solution of 4-aminomethyl piperidine (7.19 g) in anhydrous methylene chloride (80 ml), there was dropwise added a solution of benzyloxycarbonyl chloride (3.0 ml) in anhydrous methylene chloride (25 ml) under a nitrogen gas atmosphere while cooling with dry ice-methanol. After the completion of the dropwise addition, the resulting mixture was stirred while cooling with dry ice-methanol for 20 minutes and then stirred at room temperature for additional 2 hours. The reaction solution was concentrated under reduced pressure and ether and a citric acid solution were added to the resulting residue. The resulting aqueous phase was washed twice with ether. After addition of chloroform to the aqueous phase, sodium carbonate was added thereto at room temperature with stirring to make the aqueous phase basic. Separately, the resulting organic phase was washed with saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting oily product was dissolved in ether and a 4N hydrogen chloride solution in ethyl acetate (10 ml) was added to the ether solution with ice cooling. The resulting precipitates were filtered off to thus give the title compound (Reference Compound 4-1, 1.86 g) in the form of crystals.

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