(R)-5-dibenzylamino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole → (R)-5-Amino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-5-dibenzylamino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole (1.08 g, 2.64 mmol) and 20% palladium hydroxide on carbon (0.6 g) in absolute ethanol (25 mL) was shaken under a hydrogen atmosphere (3 atm) at 40 °C. for 4 hours. The resulting mixture was filtered through diatomaceous earth, and the filtrate was evaporated under reduced pressure to afford the title compound (0.60 g, 2.62 mmol, 99%) as a white foam: 1H NMR (DMSO-d6) δ 10.65 (br s, NH), 7.14 (d, J=2.2 Hz, 1H), 7.12 (d, J=8.6 Hz, 1H), 6.85 (d, J=1.6 Hz, 1H), 6.60 (dd, J=2.0 and 8.6 Hz, 1H), 3.63-2.83 (m, 7H), 2.78 (s, 3H), 2.05-1.67 (m, 4H); [α]25 =+9° (MeOH, c=1.0); HRMS calculated for C14H19N3: 229.1575; found: 229.1593.

Provenance & Evidence