Hydrochloric Acid → 3,3-Dimethyl-6-morpholinoindoline

Participants

Reaction Steps

1-(3,3-Dimethyl-6-morpholinoindolin-1-yl)ethanone was dissolved in acetonitrile (100 mL) and treated with 5 N HCl (50 mL) at 95° C. After 2 h, the mixture was cooled to rt. The reaction was carefully neutralized with saturated NaHCO3 solution to pH 10 and extracted with EtOAc (100 mL×4). The combined organics were washed with water, brine, dried, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (EtOAc/hexane, 0/1 to 1/0) to give 4-(3,3-dimethylindolin-6-yl)morpholine as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 6.80 (1H, d, J=7.8 Hz), 6.14 (1H, dd, J=8.0, 2.2 Hz), 6.09 (1H, d, J=2.0 Hz), 5.28 (1H, s), 3.65-3.73 (4H, m), 3.13 (2H, d, J=2.0 Hz), 2.92-2.99 (4H, m), 1.17 (6H, s). Mass Spectrum (ESI) m/e=233.2 (M+1).

Provenance & Evidence