Aluminium lithium hydride → [3-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-diethylamine

HRID 24341Notes

Reaction equation

HRID 24341 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1([CH3:27])[CH2:16][C:15]2[NH:14][CH:13]=[C:12]([CH2:17][CH2:18][C:19]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=O)[C:11]=2[C:10](=O)[CH2:9]1>C1COCC1.[OH-].[Na+].O>[CH3:27][C:8]1([CH3:7])[CH2:16][C:15]2[NH:14][CH:13]=[C:12]([CH2:17][CH2:18][CH2:19][N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[C:11]=2[CH2:10][CH2:9]1

Participants

6

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 225710523-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-N,N-diethylpropionamide

Product 1

HCID 22571045[3-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-diethylamineYield 90.2%

Reagents, catalysts & solvents 3

HCID 14798Sodium HydroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LAH (0.57 g, 15.1 mmol) was added dropwise to a suspension of 3-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-N,N-diethylpropionamide (1.1 g, 3.8 mmol) in THF (80 mL). The mixture was refluxed overnight. The reaction was cooled and ice was added until no more gas was generated. A few drops of 15% NaOH in water was then added. The mixture was stirred at room temperature for 30 minutes and then filtered to remove insolubles. The filtrate was concentrated to give 0.9 g of [3-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-diethyl-amine as a light yellow oil.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. temperatureThe reaction was cooled
  3. additionice was added until no more gas
  4. filtrationfiltered
  5. customto remove insolubles
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-dd9e968ca85d42c8a2906b83d71b609b
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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