1-(2-(1-Methylpyrrolidin-2-yl)ethyl)-7-nitro-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one → 7-Amino-1-(2-(1-methylpyrrolidin-2-yl)ethyl)-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one

Participants

Reaction Steps

A solution of 2 (600 mg, 1.89 mmol) in dry ethanol (10 mL) was treated with Pd—C (˜0.06 g) and purged with hydrogen gas. The reaction mixture was stirred at room temperature under hydrogen atmosphere (balloon pressure) overnight (18 h). The mixture was filtered through a celite bed and washed with methanol (3×25 mL). The combined organic fractions were concentrated to give a brown residue. The product was purified by dry column chromatography (2 N NH3 in MeOH:CH2Cl2, 5:95) to give compound 3 (435 mg, 80%) as a colourless foam. 1H-NMR (DMSO-d6, 300 MHz) δ: 1.29-1.38 (m, 2H), 1.54-1.60 (m, 2H), 1.66-1.82 (m, 2H), 1.89-2.10 (m, 10H), 2.38-2.45 (m, 2H), 2.84-2.91 (m, 1H), 5.07 (brs, 2H), 6.36-6.52 (m, 2H), 6.85-6.98 (m, 1H).

Provenance & Evidence