Aluminium lithium hydride → HCID 22561922, compound

HRID 1839591Notes

Reaction equation

HRID 1839591 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH:7]1[C:15]2[C:10](=[C:11]([C:16]3[CH:17]=[C:18]([CH2:22][C:23]([N:25]([CH3:27])[CH3:26])=O)[CH:19]=[CH:20][CH:21]=3)[CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1>C1COCC1>[NH:7]1[C:15]2[C:10](=[C:11]([C:16]3[CH:17]=[C:18]([CH2:22][CH2:23][N:25]([CH3:26])[CH3:27])[CH:19]=[CH:20][CH:21]=3)[CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22561956HCID 22561956, compound

Product 1

HCID 22561922HCID 22561922, compoundYield 134.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LAH (276 mg, 7.2 mmol) in THF (20 mL) under nitrogen at rt was added dropwise a solution of 2-[3-(1H-indol-4-yl)-phenyl]-N,N-dimethyl-acetamide (500 mg, 1.8 mmol) in THF (10 mL). After stirring at rt for 6 hours, the reaction was quenched with water (0.6 mL) dropwise. The precipitate was filtered off, washed with ethyl acetate (3×), the filtrate was concentrated t give 640 mg of {2-[3-(1H-indol-4-yl)-phenyl]-ethyl}-dimethyl-amine.

Workup

  1. customthe reaction was quenched with water (0.6 mL) dropwise
  2. filtrationThe precipitate was filtered off
  3. washwashed with ethyl acetate (3×)
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-efd1029685c14a338772f1119253fdc3
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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