Dimethylamine → HCID 10608272, compound

HRID 1069559Notes

Reaction equation

HRID 1069559 reaction equation
[CH2:1]=O.[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[CH:8]2.[CH3:14][NH:15][CH3:16].O>O1CCCC1>[CH3:14][N:15]([CH2:1][N:10]1[C:11]2[C:7](=[CH:6][C:5]([O:4][CH3:3])=[CH:13][CH:12]=2)[CH:8]=[CH:9]1)[CH3:16]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 962WaterHCID 138725-Methoxyindole

Product 1

HCID 10608272HCID 10608272, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 37% aqueous solution of formaldehyde (11 g, 0.176 mol) was added dropwise to 10 g (0.068 mol) of 5-methoxy-1H-indole and 17 mL (0.176 mol) of 40% aqueous dimethylamine in 100 mL of tetrahydrofuran and the mixture heated to maintain reflux for 3 hours. After cooling water was added and the mixture extracted with EtOAc. The EtOAc solution was washed twice with water, dried (Na2SO4), and concentrated at reduced pressure. The residue was chromatographed on silica eluting with a gradient, CH2Cl2→2% MeOH/CH2Cl2, to give 6.26 g (45% yield) of 1-dimethylaminomethyl-5-methoxy-1H-indole as an oil.

Workup

  1. temperaturethe mixture heated
  2. temperatureto maintain
  3. temperaturereflux for 3 hours
  4. additionwas added
  5. extractionthe mixture extracted with EtOAc
  6. washThe EtOAc solution was washed twice with water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated at reduced pressure
  9. customThe residue was chromatographed on silica eluting with a gradient, CH2Cl2

Sources & evidence

ORD record
ord-012ee7d804a74402927ae1bd7a020b8d
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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