Water → HCID 86746359, compound

HRID 1647242Notes

Reaction equation

HRID 1647242 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH:23]([CH3:26])[CH2:24][Cl:25].O>CN(C)C=O>[CH3:1][N:2]([CH:24]([Cl:25])[CH:23]([CH3:26])[CH3:22])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 77039N-MethylhomoveratrylamineHCID 955661-Bromo-3-chloro-2-methylpropane

Product 1

HCID 86746359HCID 86746359, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8.0 g of N-methyl-(2-(3,4-dimethoxyphenyl)ethyl)amine was dissolved in 120 ml of N,N-dimethylformamide, followed by the addition of 6.8 g of anhydrous potassium carbonate and 14.4 ml of 1-bromo-3-chloro-2-methylpropane. The obtained mixture was reacted at a room temperature for 12 hours, followed by the addition of water. The obtained mixture was extracted with ethyl acetate. The ethyl acetate phase was washed with water and a saturated aqueous solution of common salt, dried over anhydrous potassium carbonate and distilled to remove the solvent. The obtained residue was purified by silica gel column chromatography [solvent: dichloromethane/methanol (50:1)] to obtain 4.67 g of the title compound as a pale yellow oil (yield : 40%).

Workup

  1. customThe obtained mixture was reacted at a room temperature for 12 hours
  2. extractionThe obtained mixture was extracted with ethyl acetate
  3. washThe ethyl acetate phase was washed with water
  4. dry with materiala saturated aqueous solution of common salt, dried over anhydrous potassium carbonate
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe obtained residue was purified by silica gel column chromatography [solvent: dichloromethane/methanol (50:1)]

Sources & evidence

ORD record
ord-e25b7bc3673248abab449e276c8e685f
Source dataset
uspto-grants-1995_07
Patent number
US05430059

Reaction notes

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