Methylamine → 1-Methyl-3-(methylaminomethyl)indole

HRID 18227

Reaction equation

HRID 18227 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=O)=[CH:3]1.[CH3:13][NH2:14].[BH4-].[Na+]>CO>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][NH:14][CH3:13])=[CH:3]1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 878941-Methyl-1H-indole-3-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 109867781-Methyl-3-(methylaminomethyl)indole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 1-methylindole-3-carboxaldehyde (10.0 g, 62.8 mmole) in MeOH (100 mL) was added a solution of 2.0 M CH3NH2 in MeOH (126 mL, 252.0 mmole). The reaction was stirred at RT for 2 hrs, then was concentrated to a light yellow oil. This oil was dissolved in EtOH (300 mL), and NaBH4 (2.38 g, 62.8 mmole) was added. After 2 hrs the reaction was concentrated to a slurry and dissolved in 1.0 N NaOH (75 mL). The aqueous solution was extracted with Et2O (2×200 mL) and the combined organic fractions were dried over Na2SO4 and concentrated. Flash chromatography on silica gel (9:1 CHCl3/MeOH containing 5% NH4OH) and drying in high vacuum left the title compound (10.1 g, 92%) as a faintly yellow oil: MS (ES) m/e 175 (M+H)+.

Workup

  1. concentrationwas concentrated to a light yellow oil
  2. dissolutionThis oil was dissolved in EtOH (300 mL)
  3. concentrationAfter 2 hrs the reaction was concentrated to a slurry
  4. dissolutiondissolved in 1.0 N NaOH (75 mL)
  5. extractionThe aqueous solution was extracted with Et2O (2×200 mL)
  6. dry with materialthe combined organic fractions were dried over Na2SO4
  7. concentrationconcentrated
  8. customFlash chromatography on silica gel (9:1 CHCl3/MeOH containing 5% NH4OH) and drying in high vacuum
  9. waitleft the title compound (10.1 g, 92%) as a faintly yellow oil

Sources & evidence

ORD record
ord-91ebed200773476eb1e380408676ffd3
Source dataset
uspto-grants-2010_06
Patent number
US07741339B2

Linked notes

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