2-Dimethylaminopyridine → 1-Benzyl-piperidin-4-yl 2-dimethylamino-benzoate

Participants

Reaction Steps

0.33 g (0.002 mol) of 2-dimethylaminobenzoic acid was dissolved in 10 ml of dimethylformamide, treated with 0.122 g (0.001 mol) of dimethylaminopyridine and 0.383 g (0.002 mol) of 1-benzyl-4-hydroxypiperidine and cooled to 0°. 0.422 g (0.0022 mol) of N-ethyl-N'-(3-dimethylaminopropyl)-carbodiimide hydrochloride was added and the mixture was stirred at 0° for a further 2 hrs. Subsequently, the mixture was stirred at room temperature for 3 days, the solvent was distilled off and the residue was chromatographed on silica gel with ethyl acetate/hexane (1:2). 0.31 g (46%) of 1-benzyl-piperidin-4-yl 2-dimethylamino-benzoate was obtained as a colorless oil.

Provenance & Evidence