Benzoyl chloride → 1-Benzylpiperidin-4-ylmethyl benzoate

Participants

Reaction Steps

0.248 g (0.00121 mol) of 1-benzyl-4-hydroxymethyl-piperidine was dissolved in 5 ml of toluene and treated with 0.2 ml (0.00145 mol) of triethylamine and 0.155 ml (0.00133 mol) of benzoyl chloride. The mixture was boiled at reflux for 18 hrs., the solvent was distilled off and the residue was taken up in ether. The organic phase was washed with water and saturated sodium chloride solution and dried over magnesium sulfate. It was concentrated and the residue was chromato-graphed on silica gel with ethyl acetate/hexane (1:1) as the eluent. 0.2 g (53%) of 1-benzylpiperidin-4-ylmethyl benzoate was obtained as a yellow oil. MS: me/e (% basic peak)=309 (C20H23NO2+, 18), 308 (17), 232 (14), 204 (41), 159 (18.6), 105 (25.5), 91 (100).

Provenance & Evidence