Aluminium lithium hydride → [5-(3-diethylamino-propyl)-1H-indol-2-yl]-methanol

HRID 1790903Notes

Reaction equation

HRID 1790903 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH2:15][CH2:16][CH2:17][N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:10][CH:9]=2)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:21]([N:18]([CH2:19][CH3:20])[CH2:17][CH2:16][CH2:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:4][OH:3])=[CH:14]2)[CH3:22]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 695872925-(3-Diethylamino-propyl)-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 22042151[5-(3-diethylamino-propyl)-1H-indol-2-yl]-methanolYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-(3-Diethylamino-propyl)-1H-indole-2-carboxylic acid ethyl ester (1.2 g, 3.97 mmol) in tetrahydrofuran (48 mL) was added dropwise to the lithium aluminum hydride (602 mg, 15.87 mmol) stirred in tetrahydrofuran (30 mL) under nitrogen. After stirring for 2 hours, the reaction was quenched in water (0.6 mL), 15% sodium hydroxide (0.6 mL) and then water (1.8 mL). The mixture was stirred overnight. The precipitate was filtered off and the filtrate was concentrated to give 680 mg (66%) of [5-(3-diethylamino-propyl)-1H-indol-2-yl]-methanol.

Workup

  1. customthe reaction was quenched in water (0.6 mL)
  2. stirringThe mixture was stirred overnight
  3. filtrationThe precipitate was filtered off
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-16b86cd36dd247ae86be41aa20a89b40
Source dataset
uspto-grants-2006_07
Patent number
US07071332B2

Reaction notes

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