Aluminium lithium hydride → 1H-indole-3-propylamine

HRID 555335

반응식

HRID 555335 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][NH-:13])=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][NH2:13])=[CH:2]1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 866356103-(1H-indol-3-yl)propylamide

생성물 1

HCID 289891H-indole-3-propylamine수율 94%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To the solution of 3-(1H-indol-3-yl)propylamide (1.85 g, 9.83 mmol) in tetrahydrofuran (50 mL) is added lithium aluminum hydride (1.49 g, 39.31 mmol) at 0° C. The resulting mixture is warmed to room temperature and then refluxed for 2.5 hours. The mixture is then cooled to room temperature and quenched by slow addition of water (2 mL) followed by aqueous 15% sodium hydroxide (2 mL) and water (2 mL). The mixture is allowed to stir overnight and filtered through celite. The filtrate obtained is evaporated and the residue is subjected to flash column chromatography (50% dichloromethane: 40% methanol: 10% aqueous ammonia (40%)) to afford 3-(1H-Indol-3-yl)propylamine (1.61 g, 94%).

후처리

  1. temperaturerefluxed for 2.5 hours
  2. temperatureThe mixture is then cooled to room temperature
  3. customquenched by slow addition of water (2 mL)
  4. filtrationfiltered through celite
  5. customThe filtrate obtained
  6. customis evaporated

출처 및 근거

ORD 기록
ord-b7faf9f2702845409cf1274eab15ff82
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08053442B2

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