3-(4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid dimethyl amide → 3-(3-dimethylaminopropyl)-4,5,6,7-tetrahydro-1H-indole

Participants

Reaction Steps

3-(4,5,6,7-Tetrahydro-1H-indol-3-yl)-propionic acid dimethyl amide (7.7 g) and 13 g of borane-tetrahydrofuran complex in 50 mL of tetrahydrofuran was refluxed for 3 hours. The reaction was quenched with acetone and then water and evaporated to dryness. The residue was chromatographed on silica gel to give 2 g (20% yield) of 3-(3-dimethylamino-propyl)-4,5,6,7-tetrahydro-1H-indole as a yellow oil.

Provenance & Evidence