Water → methyl((1-methyl-1H-indol-2-yl)methyl)amine

HRID 1601073Notes

Reaction equation

HRID 1601073 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]([NH:19][CH3:20])=O.O>C1COCC1>[CH3:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH2:17][NH:19][CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 12303315N,1-dimethylindole-2-carboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amineYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LAH (50 mL, 1M solution in THF) was added dropwise through a syringe to a solution of 1-methyl-2-(methylaminocarbonyl)indole (2.33 g, 12.4 mmol) in anhydrous THF (10 mL) with cooling, and the resulting solution was stirred at RT under argon overnight. H2O was added dropwise with cooling to destroy excess LAH, and the colorless precipitate was removed by filtration and washed with THF. The filtrate was dried (K2CO3), concentrated, and purified by silica gel flash chromatography to afford the title compound (430 mg, 20% yield) as a yellow solid. MS (ES) m/e 175 (M+H)+.

Workup

  1. temperaturewith cooling
  2. temperaturewith cooling
  3. customto destroy excess LAH
  4. customthe colorless precipitate was removed by filtration
  5. washwashed with THF
  6. dry with materialThe filtrate was dried (K2CO3)
  7. concentrationconcentrated
  8. custompurified by silica gel flash chromatography

Sources & evidence

ORD record
ord-788d2e1b4aa5436e8e85015549b87f32
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

Loading…