Aluminium lithium hydride → 3-(1H-indol-2-yl)propan-1-amine

HRID 1954227Notes

Reaction equation

HRID 1954227 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][CH2:11][C:12]([NH2:14])=O.[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)[CH:3]=[C:2]1[CH2:10][CH2:11][CH2:12][NH2:14]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21703095HCID 21703095, compound

Product 1

HCID 223118203-(1H-indol-2-yl)propan-1-amineYield 92.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-indolyl-propionamide (5 g, 24.7 mmol) in tetrahydrofuran anhydrous (150 ml) was added lithium aluminum hydride (1.0 M solution in tetrahydrofuran; 100 ml) slowly. The reaction mixture was refluxed for 3 hours, then was quenched by adding water (4 ml), 15% sodium hydroxide (4 ml) and water (12 ml) at 0° C. The mixture was filtered through celite and concentrated under vacuum. Chromatography (10% methanol-methylene chloride plus ammonium hydroxide) afforded 4.0 g (86%) of product as a white solid: mp 58-60.5° C. MS EI m/e 174 (M·+).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. customwas quenched
  3. additionby adding water (4 ml), 15% sodium hydroxide (4 ml) and water (12 ml) at 0° C
  4. filtrationThe mixture was filtered through celite
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f64654af3991487a957b77052455ccfb
Source dataset
uspto-grants-2000_09
Patent number
US06121307

Reaction notes

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