2-(1H-indol-3-yl)propanenitrile → beta-Methyltryptamine

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of LAH (3.4 g, 90 mmol) in THF (40 mL, anhyd) chilled to 0° C. was added a solution of 2-(1H-indol-3-yl)propionitrile (2.5 g, 14.7 mmol) in THF (40 mL, anhyd). The reaction mixture was allowed to warm to ambient temperature and then heated at reflux. After 1 h the reaction mixture was cooled to 0° C. and quenched cautiously with wet THF (5-10% H2O) until gas evolution had ceased. The resulting mixture was filtered through Celite™ and concentrated to give a brown residue. The filtering agent was rinsed with Et2O (100 mL), which was combined with the residue, dried (Na2SO4), and concentrated under reduced pressure to yield the title compound (2.1 g, 82%) as a pale amber oil. 1H-NMR (CDCl3): δ 8.28 (1 H, br s), 7.61 (1H, d), 7.36 (1H, d), 7.16 (1H, app t), 7.08 (1H, app t), 6.96 (1H, br s), 3.41 (2H, br s), 3.19 (1H, q), 2.95 (2H, app d), 1.35 (3H, d).

Provenance & Evidence