Aluminium lithium hydride → [3-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-diethylamine

Participants

Reaction Steps

LAH (0.57 g, 15.1 mmol) was added dropwise to a suspension of 3-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-N,N-diethylpropionamide (1.1 g, 3.8 mmol) in THF (80 mL). The mixture was refluxed overnight. The reaction was cooled and ice was added until no more gas was generated. A few drops of 15% NaOH in water was then added. The mixture was stirred at room temperature for 30 minutes and then filtered to remove insolubles. The filtrate was concentrated to give 0.9 g of [3-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-diethyl-amine as a light yellow oil.

Provenance & Evidence