Triethylamine → Ethyl 2-(1-methyl-4-(5-phenethylfuran-2-carboxamido)piperidin-4-yl)acetate

Participants

Reaction Steps

A stirred solution of ethyl 2-(4-amino-1-methylpiperidin-4-yl)acetate (16 mg, 0.077 mmol) in CH2Cl2 (1 mL) was treated with NEt3 (31 uL, 0.219 mmol), and 2,5-dioxopyrrolidin-1-yl 5-phenethylfuran-2-carboxylate, prepared as described in Preparation 5 (23 mg, 0.073 mmol). The reaction was stirred overnight, at room temperature, then the solvent removed in vacuo and the crude product purified by column chromatography to obtain the title compound (25 mg, 86%). 1H NMR (400 MHz, CD3OD) δ 7.29-7.16 (m, 5H), 7.00 (s, 1H), 6.17 (s, 1H), 4.06 (q, 2H, J=7.2 Hz), 3.05 (s, 4H), 2.88 (s, 2H), 2.75-2.69 (m, 2H), 2.54-2.48 (m, 2H), 2.41-2.31 (m, 5H), 1.87-1.81 (m, 2H), 1.15 (t, 3H, J=7.2 Hz); MS ESI 399.2 [M+H]+, calcd for [C23H30N2O4+H]+ 399.50.

Provenance & Evidence