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

HRID 1946553Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1946553
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 289891H-indole-3-propylamineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7dc7683f3f1d4485888a4e89db72624c
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399453B2

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