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

HRID 1666871Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[Al+3].[Cl-].[Cl-].[Cl-].[F:11][C:12]([F:28])([F:27])[C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[C:16]2[C:22](=O)[C:23]([NH2:25])=O.[OH-].[Na+]>C1COCC1>[F:27][C:12]([F:11])([F:28])[C:13]1[CH:14]=[C:15]2[C:19]([NH:18][CH:17]=[C:16]2[CH2:22][CH2:23][NH2:25])=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 5 °C

Procedure

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 5-1° 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 warning 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.

Workup

temperaturecooling
temperaturewhile maintaining the temperature at less than about 30° C
stirringAfter stirring for about 30 minutes
filtrationfilter
washwash with THF (2 L)
customevaporate the filtrate

Sources & evidence

ORD record: ord-d913e9b96aec4c63b59e12884642049c
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044090B2

Reaction notes

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