Sodium Hydroxide → 2-(5-(trifluoromethyl)-1H-indol-3-yl)ethanamine

Participants

Reaction Conditions

Reaction Steps

Add LiAlH4 (37.95 g, 1.00 mol) to THF (650 mL) under ice-bath cooling. Prepare a solution of AlCl3 (50 g, 375 mmol) in THF (600 ml) and add dropwise to the LiAlH4 solution over 45 min at 5–10° C. While maintaining the temperature at about 5° C., add a solution of 2-(5-(trifluoromethyl)-1H-indol-3-yl)-2-oxo-acetamide (21.4 g, 83.5 mmol) in THF (600 ml) and stir overnight with warming to ambient temperature. Cool the mixture with ice water and treat with 30% NaOH (100 ml) while maintaining the temperature at less than about 30° C. After stirring for about 30 minutes, filter, wash with THF (2 L), and evaporate the filtrate to give the title compound. Form of the HCl salt by dissolving the title compound in diethyl ether and adding of a solution of HCl in diethyl ether (until acidic). Collect the solid by filtration, wash with diethyl ether, and dry under reduced pressure to give the hydrochloride salt of the title compound.

Provenance & Evidence