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

HRID 555335

Reaction equation

HRID 555335 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 289891H-indole-3-propylamineYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-b7faf9f2702845409cf1274eab15ff82
Source dataset
uspto-grants-2011_11
Patent number
US08053442B2

Linked notes

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