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

HRID 1666871노트

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HRID 1666871 반응식
[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

참가 물질

6

반응물 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 210714242-(5-(trifluoromethyl)-1H-indol-3-yl)-2-oxo-acetamideHCID 21226445Aluminium lithium hydride2회

생성물 1

HCID 120301362-(5-(trifluoromethyl)-1H-indol-3-yl)ethanamine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
5 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-d913e9b96aec4c63b59e12884642049c
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044090B2

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