Dimethylformamide → Tert-butyl 4-(1-(3-(cyclopropylmethoxy)-5-methoxybenzamido)ethyl)piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of 3-(2-cyclopropylethyl)-5-methoxybenzoic acid (2.4 g, 10.7 mmol) and tert-butyl 4-(1-aminoethyl)piperidine-1-carboxylate (2.4 g, 10.7 mmol) in DMF (40 ml), was added triethyl amine (4.47 ml). After stirring for 10 minutes at room temperature TBTU (5.15 g, 16.1 mmol) was added in portions. The reaction mixture was stirred at room temperature for 2 hours. 100 ml H2O was added and the product was extracted into ethyla acetate. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by using normal phase chromatography eluting with petroleum ether containing 10% ethyl acetate to give tert-butyl 4-(1-(3-(cyclopropylmethoxy)-5-methoxybenzamido)ethyl)piperidine-1-carboxylate (3.0 g).

Provenance & Evidence