Tryptamine → 2-[2-(1H-indol-3-yl)ethyl]-1H-Isoindole-1,3(2H)-dione

Participants

Reaction Steps

To a stirred suspension of 2-(1H-indol-3-yl)ethylamine (2.0 g in 20 mL of dry tetrahydrofuran) was added N-carbethoxyphthalimide (2.85 g) and the mixture heated to reflux on an oil bath. After 48 hours the reaction was cooled to room temperature, filtered and the filtrate concentrated in vacuo. The resulting solid was suspended in a mixture of hexane/methylene chloride (2.5:1) and filtered. Purification of the collected solids by flash chromatography (methylene chloride:methanol, 97:3) gave the title compound (3.1 g).

Provenance & Evidence