5-Phenoxy-1H-indole-3-ethanamine → HCID 21071537, compound

Participants

Reaction Steps

Combine 5-phenoxytryptamine (0.400 g, 1.59 mmol), 3-phenoxybenzaldehyde (0.377 g, 1.90 mmol) and molecular sieves 4 Å (0.40 g) in methanol (15 mL) and stir for 4 h. Filter and wash the molecular sieves several times with MeOH. Add NaBH4 (61.5 mg, 1.59 mmol) in portions to the filtrate and stir at room temperature for 1 h. Remove the MeOH under vacuum to give a residue, dilute the residue with dichloromethane/water, separate the layers, extract the aqueous layer with dichloromethane, combine the organic layers, and dry over Na2SO4. Concentrate in vacuo and chromatograph on silica gel eluting with dichloromethane/MeOH the title compound. Form the oxalate salt of the title compound: m.p. 196-198° C.; 1H NMR (300 MHz, DMSO-d6) 2.95-3.15 (m, 4H), 4.15 (s, 2H), 6.85-7.46 (m, 18H), 11.06 (br, 1H); MS (ELECTROSPRAY) m/e: 435.3 (M+1); HRMS (ES+) calcd for C29H27N2O2 (M+H) 435.2084 found 435.2073.

Provenance & Evidence