Acetamide, N-(2-(5-methoxy-2-methyl-3-indolyl)ethyl)- → N-[2-(5-Methoxy-2-methyl-1H-indol-3-yl)ethyl]cyclopropanecarboxamide

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Reaction Steps

A solution of the crude 2-methyl-5-methoxytryptamine (from 5 mmol of 3a), in THF (15 mL) and TEA (0.7 mL) was acylated with cyclopropanecarbonyl chloride (0.45 mL) at room temperature for 1.5 h using the procedure described for 4a. The desired product 4e was obtained as white solid (0.615 g, 45% overall yield), mp 102°-103° C. IR νmax : 3460, 3300, 1650. 1H NMR: 0.70(m, 2H, CH2cyclopropyl), 0.97(m, 2H, CH2 cyclopropyl), 1.24(m, 1H, cyclopropyl-CH), 2.36(s, 3H, 2-CH3), 2.90(t, 2H, β -CH2), 3.51(q, 2H, α-CH2), 3.85(s, 3H, OCH3), 5.75(br s, 1H, NH), 6.75-7.25 (m, 3Harom), 8.00(br s, 1H, NHindole).

Provenance & Evidence