Benzyl Bromide → HCID 15892976, compound

Participants

Reaction Steps

0.574 g (0.003 mol) of 1-benzyl-4-hydroxypiperidine dissolved in 5 ml of dimethylformamide was added dropwise at 0° to a suspension of 0.14 g (0.0035 mol) of sodium hydride in 5 ml of dimethylformamide. The mixture was left to warm to room temperature and was stirred for 1.5 hrs. Then, 0.39 ml (0.0033 mol) of benzyl bromide was added dropwise. The mixture was stirred at 40° for 18 hrs. The solvent was removed, the residue was taken up in water, adjusted to pH 11 with 2N aqueous NaOH and extracted with ether. The organic phase was dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel with ethyl acetate/hexane (1:1) as the eluent. 0.333 g (40%) of 1-benzyl-4-benzyloxypiperidine was obtained as a yellow oil. MS: me/e=282 (C9H24NO+).

Provenance & Evidence