Hydrochloric Acid → Methyl 4-(5-hexanamidoindol-3-ylmethyl)-3-methoxybenzoate

Participants

Reaction Steps

A stirred solution of methyl 4-(5-aminoindol-3-ylmethyl)-3-methoxybenzoate (A) (0.2 g.) in dichloromethane (5 ml. ) under an atmosphere of nitrogen, was treated with N-methylmorpholine (0.25 g.), followed by hexanoyl chloride (0.103 g.). After being stirred for 2 hours, the mixture was poured into 1M hydrochloric acid (20 ml.). This mixture was extracted with ethyl acetate (2×20 ml.). The combined organic extracts were dried (MgSO4) and evaporated. The yellow oil obtained was purified by flash chromatography on silica gel (75 ml.), eluting with 6:4 v/v ethyl acetate:hexane, to give the title compound (0.24 g., 92%) as a colorless oil; NMR: 0.83(t,3H, CH2.CH3), 1.36(m,4H, CH2.CH2.CH3), 1.57(quintet,2H, CH2.CH2.CON), 2.24(t, 2H, CH2.CON), 3.80(s,3H, COOCH3), 3.90(s,3H, OCH3), 3.99(s,2H, CH2. Ar), 7.1(m, 2H), 7.21(m,2H), 7.44(m,2H), 7.69(s,1H, H4 -indole), 9.59(s,1H, CONH), 10.77(s,1H, H1 -indole).

Provenance & Evidence