Hydrochloric Acid → Methyl 4-(5-hexanamido-1-methylindol-3-ylmethyl)-3-methoxybenzoate

Participants

Reaction Steps

Hexanoylchloride (0.029 g.) was added to a stirred solution of methyl 4-(5-amino-1-methylindol-3-ylmethyl)-3-methoxybenzoate (D) (0.05 g.) and N-methylmorpholine (0.05 g.) in dichloromethane (3 ml.), under an atmosphere of nitrogen. The mixture was stirred for 2 hours and then poured into 1M hydrochloric acid (15 ml.). This mixture was extracted with ethyl acetate (2×20 ml.). The combined extracts were dried (MgSO4), and evaporated. The residual oil was purified by flash chromatography on silica gel (50 ml.), eluting with 4:6 v/v ethyl acetate:hexane, to give a colorless oil, which was crystallized from a mixture of toluene and hexane to give the title compound (0.05 g, 65%) as a white powder: NMR: 0.86 (t, 3 H, CH2.CH3), 1.28 (m,4 H, CH2.CH2.CH3), 1.57 (quintet, 2 H, CH2.CH2.CON), 2.25 (t,2 H, CH2.CH2.CON), 3.69 (s,3 H, NCH3), 3.82 (s,3 H, CO.OCH3), 3.92 (s,3 H, OCH 3), 3.97 (s, 2 H, CH2.Ar), 7.05 (s,1 H), 7.13 (d,1 H), 7.27 (d,1 H), 7.28 (d,1 H), 7.40 (dd,1 H), 7.48 (s,1 H), 7.74 (s,1 H), 9.61 (s,1 H).

Provenance & Evidence