N,1-dimethylindole-2-carboxamide → methyl((1-methyl-1H-indol-2-yl)methyl)amine

HRID 1633840Notes

Reaction equation

HRID 1633840 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[N:6]([CH3:14])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:14][N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=[C:5]1[CH2:3][NH:2][CH3:1]

Participants

4

Reactant 2

HCID 12303315N,1-dimethylindole-2-carboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amineYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of N,1-dimethylindole-2-carboxamide (23.3 g, 124.2 mmole) in dry THF (400 mL) was added LiAlH4 (1.0 M in THF, 250 mL, 250 mmole). The reaction solution was heated to 70° C. under argon for 36 hr with stirring. The resulting white cloudy solution was allowed to cool to RT and then was submitted to a basic work-up according to the procedure of Micovic and Mihailovic (Micovic, V. M.; M. L. J. J. Org. Chem. 1956, 18, 1190). Purification by chromatography on silica gel (5% NH4OH in 9:1 CHCl3/MeOH) afforded the titled compound (15.8 g, 73%) as a colorless oil: MS (ES) m/e 175 (M+H)+.

Workup

  1. temperatureto cool to RT
  2. customPurification by chromatography on silica gel (5% NH4OH in 9:1 CHCl3/MeOH)

Sources & evidence

ORD record
ord-c170b92f56994e979e5a1236971d65ba
Source dataset
uspto-grants-2003_01
Patent number
US06503903B1

Reaction notes

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