Indole → 1-benzyl-3-(methylaminomethyl)-1H-indole

HRID 1761102Notes

Reaction equation

HRID 1761102 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:20][N:21](C=O)[CH3:22]>O>[CH2:12]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:20][NH:21][CH3:22])=[CH:2]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 798IndoleHCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydride

Product 1

HCID 122838761-benzyl-3-(methylaminomethyl)-1H-indole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

3-[N-(Benzyioxycarbonyl)-N-methylaminomethyl]-1-benzyl-1H-indole NaH (60% dispersion in mineral oil, 0.15 g, 3.8 mmole) was added portionwise, allowing for gas evolution, to a solution of 3-(N-(benzyloxycarbonyt)-N-methylaminomethyl]methylaminomethyl]-1H-indole (0.7 g, 2.5 mmole) in DMF (25 mL) at 0° C. When the NaH addition was complete, benzyl bromide (1.2 nL, 10.0 mmole) was added at 0° C. The reaction was stirred at 0° C. for 15 minutes then at RT overnight. The reaction was diluted with water and extracted with ethyl acetate. The combined extracts were dried over Na2SO4 and concentrated. Flash chromatography on silica gel (33% ethyl acetate/hexanes) gave the title compound. (0.9 g, 93%) as an off white solid: MS (ES) mVe 385 (M+H)+.

Workup

  1. customat 0° C
  2. customat RT
  3. customovernight
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-08b68a6152784c058d01043516c717f5
Source dataset
uspto-grants-2005_01
Patent number
US06846819B1

Reaction notes

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