5-[2-(Dibenzylamino)-1-hydroxyethyl]-indole-7-carboxamide → 5-(1-hydroxy-2-aminoethyl)-1H-indole-7-carboxamide

Participants

Reaction Steps

A solution of 5-[2-(dibenzylamino)-1-hydroxyethyl]-indole-7-carboxamide (119.7 mg, 0.3 mmol, described above) was hydrogenated for 28 hours at atmospheric pressure and room temperature in dry methanol (12.0 mL) containing 10% palladium on carbon. The mixture was filtered and the filtrate was evaporated. Crystallization from an ethyl acetate-diethyl ether mixture gave 5-(2-amino-1-hydroxyethyl)indole-7-carboxamide: mp 88°-90° C.; and NMR (DMSO-d6) δ 2.70 (d, 2H), 2.80-3.60 (br s, 5H), 4.50 (t, 1H), 6.40 (m, 1H), 7.00-7.70 (m, 3H) and 10.75 (br s, 1H).

Provenance & Evidence