Aluminium lithium hydride → 1-Methyl-N-propyl-1H-indole-2-methanamine

HRID 1920997Notes

Reaction equation

HRID 1920997 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([NH:13][CH:14]1[CH2:16][CH2:15]1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH2:11][NH:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22593775HCID 22593775, compound

Product 1

HCID 225937581-Methyl-N-propyl-1H-indole-2-methanamineYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-methyl-N-cyclopropylindole-2-carboxamide (2.1 g, 9.8 mmole) in dry THF (40 mL) was added dropwise a solution of 1.0 M LiAlH4 in THF (2.2 mL, 22 mmole). The reaction mixture was heated at reflux overnight, then was cooled and quenched with 10% NaOH. The mixture was filtered and the filtrate was concentrated in vacuo. Flash chromatography on silica gel (5% MeOH/CHCl2) gave the title compound (0.65 g, 33%) as a viscous oil: MS (ES) m/e 203 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. temperaturewas cooled
  4. customquenched with 10% NaOH
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-dbc38e1b1e474a4589f8e24899d71be1
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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