Aluminium lithium hydride → 3-(1H-indol-2-yl)propan-1-amine

Participants

Reaction Steps

To a solution of 3-indolyl-propionamide (5 g, 24.7 mmol) in tetrahydrofuran anhydrous (150 ml) was added lithium aluminum hydride (1.0 M solution in tetrahydrofuran; 100 ml) slowly. The reaction mixture was refluxed for 3 hours, then was quenched by adding water (4 ml), 15% sodium hydroxide (4 ml) and water (12 ml) at 0° C. The mixture was filtered through celite and concentrated under vacuum. Chromatography (10% methanol-methylene chloride plus ammonium hydroxide) afforded 4.0 g (86%) of product as a white solid: mp 58-60.5° C. MS EI m/e 174 (M·+).

Provenance & Evidence