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

HRID 1883647Notes

Reaction equation

HRID 1883647 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 hydride2×

Product 1

HCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 3-liter 3-necked roundbottom flask equipped with overhead stirring was charged with N,1-dimethylindole-2-carboxamide (23.4 g, 124.6 mmole) and anhydrous THF (170 mL). The solution was stirred while a solution of LiAlH4 in THF (1.0 M, 250 mL, 250 mmole) was added via syringe. Gas was evolved during the addition of the first 50 mL of LiAlH4 solution. When the addition was complete, the resulting light yellow solution was heated at gentle reflux. After 24 hr, the reaction was cooled in ice and quenched by the sequential dropwise addition of H2O (9.5 mL), 15% NaOH (9.5 mL), and H2O (28.5 mL).

Workup

  1. customA 3-liter 3-necked roundbottom flask equipped
  2. additionwas added via syringe
  3. additionWhen the addition
  4. temperaturethe resulting light yellow solution was heated at gentle reflux
  5. temperaturethe reaction was cooled in ice
  6. customquenched by the sequential dropwise addition of H2O (9.5 mL), 15% NaOH (9.5 mL), and H2O (28.5 mL)

Sources & evidence

ORD record
ord-55e430b8bc97401786a1e1d013add3f9
Source dataset
uspto-grants-2004_07
Patent number
US06762201B1

Reaction notes

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