HCID 69488497, compound → HCID 69488974, compound

Participants

Reaction Steps

4-{[1-(Cyclohexylmethyl)-7-nitro-1H-indol-3-yl]carbonyl}-1-ethylpiperazine (200 mg, 0.5 mmol) was dissolved in methanol (10 ml) to which was added palladium (5 wt. % on activated carbon; 50 mg, cat.) as a slurry in methanol (3 ml). The system was then sealed and flushed with nitrogen before fixing a hydrogen source (balloon). The mixture was stirred at room temperature under hydrogen for 15 hours after which it was filtered through celite and concentrated. The resulting brown oil was purified by flash chromatography using 95% dichloromethane, 5% methanol as eluent to yield the title product as the free base. 1H NMR (400 MHz, CD3OD) δH 0.97-1.08 (2H, m), 1.12 (3H, t, J 7.5), 1.17-1.26 (3H, m), 1.53 (2H, d, J 12.5), 1.63-1.75)(3H m) 1.87-1.98 (1H, m), 2.44-2.55 (6H, m), 3.37 (4H, t, J 5.0), 4.20 (2H, d, J 7.5), 6.59 (1H, dd, J 7.5, 1.0), 6.93 (1H, t, J 7.5), 7.06 (1H, dd, J 8.0, 1.0), 7.39 (1H, s); EIMS: m/z=369.0 [M+H]+.

Provenance & Evidence