Hydrogen Bromide → 1-Benzyl-3-(bromomethyl)piperidine

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Reaction Steps

55.1 g (0.268 mol) of N-benzyl-3-(hydroxymethyl)-piperidine are added to 400 ml of 48% hydrobromic acid with vigorous stirring and the mixture is refluxed for 1 hour. Then hydrogen bromide is introduced to saturation point (about 1 hour), the mixture is refluxed for another hour and left to stand overnight. It is then neutralized with solid potassium carbonate whilst cooling with ice and then extracted with methylene chloride. The organic phase is dried over magnesium sulphate and concentrated by evaporation in vacuo. Yield: 52.0 g (72.2% of theory), Rf value: 0.85 (aluminium oxide neutral, eluant: methylene chloride).

Provenance & Evidence