Sodium borohydride → [(1,2-dimethyl-1H-indol-3-yl)methyl](methyl)amine

HRID 2112683Notes

Reaction equation

HRID 2112683 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]=[N:12][CH3:13])=[C:3]1[CH3:14].[BH4-].[Na+]>C(O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][NH:12][CH3:13])=[C:3]1[CH3:14]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 141422191,2-Dimethyl-3-(methyliminomethyl)-1H-indole

Product 1

HCID 10877907[(1,2-dimethyl-1H-indol-3-yl)methyl](methyl)amineYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1,2-Dimethyl-3-(methyliminomethyl)-1H-indole was taken up in ethanol (200 mL) and NaBH4 (2.6 g, 68.7 mmole) was added portionwise with stirring at RT (vigorous gas evolution). After 16 h the reaction was concentrated under vacuum, and the residue was basified with aqueous 1.0 N NaOH (200 mL). The mixture was extracted with Et2O (250 mL), and the combined Et2O extracts were washed with brine, dried (Na2SO4) and concentrated. Purification by flash chromatography on silica gel (5-10% (5% NH4OH/MeOH)/CHCl3) gave the title compound (8.47 g, 68%) as an oil which solidified in the freezer: 1H NMR (400 MHz, CDCl3) δ 7.60 (d, J=7.7 Hz, 1H), 7.29 (d, J=8.0 Hz, 1H), 7.19 (t, 1H), 7.12 (t, 1H), 3.93 (s, 2H), 3.69 (s, 3H), 2.49 (s, 3H), 2.45 (s, 3H).

Workup

  1. concentrationAfter 16 h the reaction was concentrated under vacuum
  2. extractionThe mixture was extracted with Et2O (250 mL)
  3. washthe combined Et2O extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification by flash chromatography on silica gel (5-10% (5% NH4OH/MeOH)/CHCl3)

Sources & evidence

ORD record
ord-4319f17322ba4b4c89e39d263a5ca262
Source dataset
uspto-grants-2009_04
Patent number
US07524843B2

Reaction notes

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