N,1-dimethyl-1H-indole-3-carboxamide → 1-Methyl-3-(methylaminomethyl)indole

HRID 225879Notes

Reaction equation

HRID 225879 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][NH:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH3:20])[CH:12]=1)=O>C1COCC1>[CH3:20][N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([CH2:9][NH:8][CH3:7])=[CH:12]1

Participants

4

Reactant 2

HCID 5152277N,1-dimethyl-1H-indole-3-carboxamideHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 109867781-Methyl-3-(methylaminomethyl)indoleYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of LiAlH4 in THF (1.0 M, 5.20 mL, 5.2 mmole) was slowly added via syringe to a solution of N,1-dimethyl-1H-indole-3-carboxamide (0.50 g, 2.6 mmole) in anhydrous THF (15 mL). Gas was evolved during the addition of the first 2 mL of LiAlH4 solution. When the addition was complete, the resulting light yellow solution was heated at gentle reflux. After 23 hr, the reaction was cooled in ice and quenched by the sequential dropwise addition of H2O (0.5 mL), 1.0 N NaOH (0.5 mL), and H2O (0.5 mL). The mixture was stirred for 15 min, then was filtered through celite®, and the filter pad was washed thoroughly with THF. The filtrate was concentrated and the residue was flash chromatographed on silica gel (10% MeOH/CHCl3 containing 0.5% conc. NH4OH) to afford the title compound (0.30 g, 67%) as a light yellow oil: MS (ES) m/e 175 (M+H)+.

Workup

  1. additionWhen the addition
  2. temperaturethe resulting light yellow solution was heated at gentle reflux
  3. temperaturethe reaction was cooled in ice
  4. customquenched by the sequential dropwise addition of H2O (0.5 mL), 1.0 N NaOH (0.5 mL), and H2O (0.5 mL)
  5. filtrationwas filtered through celite®
  6. washthe filter pad was washed thoroughly with THF
  7. concentrationThe filtrate was concentrated
  8. customchromatographed on silica gel (10% MeOH/CHCl3 containing 0.5% conc. NH4OH)

Sources & evidence

ORD record
ord-6f64602a96eb4dbfb8cc9fcd6e1ef08b
Source dataset
uspto-grants-2009_07
Patent number
US07557125B2

Reaction notes

Loading…