methyl 4-[2-(N-benzyloxycarbonyl-N-methylamino)ethylamino]benzoate → Methyl 4-{[2-(methylamino)ethyl]amino}benzoate

Participants

Reaction Steps

To a stirred solution of methyl 4-[2-(N-benzyloxycarbonyl-N-methylamino)ethylamino]benzoate (1.26 g, 3.68 mmol) in MeOH(20 mL) was added 5 wt. Pd—C (700 mg), and the mixture was hydrogenated (3 atm) for 4 hr at room temp. The mixture was filtered, and the filtrate was evaporated under a reduced pressure to give 600 mg (78%) methyl 4-[2-(N-methylamino) ethylamino]benzoate as a colorless oil. 1H-NMR (CDCl3, 400 MHz) δ 2.46 (s, 3H), 2.88 (t, 2H, J=5.5 Hz), 3.27 (br s, 2H), 3.85 (s, 3H), 6.57 (d, 2H, J=8.8 Hz), 7.85 (d, 2H, J=8.8 Hz); MS (FAB) m/z 209 (M++1).

Provenance & Evidence