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

HRID 1761081Notes

Reaction equation

HRID 1761081 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](C(OC)=O)=[CH:2]1.[H-].[Na+].CI.[CH3:18][N:19]([CH:21]=O)[CH3:20]>O>[CH3:18][N:19]1[C:20]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:2][NH:1][CH3:9])=[CH:21]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 589098Methyl indole-3-carboxylate

Product 1

HCID 109867781-Methyl-3-(methylaminomethyl)indoleYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 1-methyl-1H-indole-3-carboxylate NaH (60% dispersion in mineral oil, 8.56 g, 214.0 mmole) was added portionwise, allowing for gas evolution, to a solution of methyl 1H-indole-3-carboxylate (25.00 g, 142.7 mmole) in DMF (350 mL) at 0° C. When the NaH addition was complete, methyl iodide (44.4 mL, 713.5 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 K2CO3 and concentrated to afford the title compound (26.00 g, 96%) as an orange solid: MS (ES) m/e 190 (M+H)+.

Workup

  1. customat RT
  2. customovernight
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined extracts were dried over K2CO3
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b602060eb656436293ef01a7aa8851ac
Source dataset
uspto-grants-2005_01
Patent number
US06846819B1

Reaction notes

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