Triethylamine → 1-Benzyl-piperidin-4-yl 3-methoxy-benzoate

Participants

Reaction Steps

1.41 g (0.00733 mol) of 1-benzyl-4-hydroxypiperidine and 1.8 ml (0.0129 mol) of triethylamine were dissolved in 50 ml of toluene and treated with 0.79 ml (0.00586 mol) of 3-methoxy-benzoyl chloride. The mixture was boiled at reflux for 2 hrs., the precipitate was filtered off and the filtrate was concentrated. The residue was chromatographed over silica gel with ethyl acetate/hexane (1:3→1:2→1:1)). 1.52 g (80%) of 1-benzyl-piperidin-4-yl 3-methoxy-benzoate were obtained as a yellowish oil. MS: me/e (% basic peak)=325 (C20H23NO3+, 7.6), 248 (4), 173 (30.3), 135 (13), 91 (78), 82 (100).

Provenance & Evidence