Methylamine → N-Methyl-N-[(2-methyl-1H-indol-3-yl)methyl]amine

HRID 18228

Reaction equation

HRID 18228 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]=O)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:13][NH2:14].[BH4-].[Na+]>CO>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][NH:14][CH3:13])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 6329MethylamineHCID 731663-Formyl-2-methylindoleHCID 4311764Sodium borohydride

Product 1

HCID 10954023N-Methyl-N-[(2-methyl-1H-indol-3-yl)methyl]amineYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 2-methylindole-3-carboxaldehyde (10.00 g, 62.84 mmole) in MeOH (100 mL) was added 2 M CH3NH2 in MeOH (200 mL). After stirring for 3 hours at RT, the reaction solution was concentrated to a yellow oil which solidified under vacuum. This solid was dissolved in ethanol (350 mL) and NaBH4 (2.38 g, 62.8 mmole) was added. The reaction was stirred at RT for 6 hours, then was concentrated under vacuum. The remaining residue was diluted with saturated aqueous Na2CO3 (50 mL) and extracted with EtOAc (2×200 mL). The organic phase was separated, washed with brine, and dried over Na2SO4. Flash chromatography on silica gel (9:1 CHCl3/MeOH containing 5% NH4OH) and drying under high vacuum gave the title compound (6.88 g, 63%) as a faintly yellow viscous solid: MS (ES) m/e 175 (M+H)+.

Workup

  1. concentrationthe reaction solution was concentrated to a yellow oil which
  2. dissolutionThis solid was dissolved in ethanol (350 mL)
  3. stirringThe reaction was stirred at RT for 6 hours
  4. concentrationwas concentrated under vacuum
  5. additionThe remaining residue was diluted with saturated aqueous Na2CO3 (50 mL)
  6. extractionextracted with EtOAc (2×200 mL)
  7. customThe organic phase was separated
  8. washwashed with brine
  9. dry with materialdried over Na2SO4
  10. customFlash chromatography on silica gel (9:1 CHCl3/MeOH containing 5% NH4OH) and drying under high vacuum

Sources & evidence

ORD record
ord-53d950d90541411399039216f0d61e5c
Source dataset
uspto-grants-2010_06
Patent number
US07741339B2

Linked notes

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