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

HRID 1371943Notes

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 5–10° 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.

Workup

temperaturecooling
temperaturewith warming to ambient temperature
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-0a78fb6f27584e91b029766293f8c614
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157488B2

Reaction notes

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