Potassium Carbonate → HCID 15754163, compound

HRID 1461663Notes

Reaction equation

HRID 1461663 reaction equation
[CH3:1][C:2]([NH2:10])([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21][CH3:22])=[O:20]>C(#N)C>[CH3:1][C:2]([NH:10][CH2:18][C:19]([O:21][CH3:22])=[O:20])([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 68509Cumylamine

Product 1

HCID 15754163HCID 15754163, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

13.5 g (0.1 mol) of α,α-dimethylbenzylamine was dissolved in 200 ml of acetonitrile, and 15 g (0.11 mol) of potassium carbonate was added thereto. 15.3 g (0.1 mol) of methyl bromoacetate was gradually dropwise added thereto under cooling with ice. After completion of the dropwise addition, reaction mixture was returned to room temperature and stirred for one day and night. Salts were removed by filtration, and acetonitrile was distilled off under reduced pressure. Water was added to the residue and extracted with ethyl acetate. The ethyl acetate layer was thoroughly washed with water and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was subjected to distillation to obtain 12.1 g (yield: 60%) of the desired compound.

Workup

  1. temperatureunder cooling with ice
  2. additionAfter completion of the dropwise addition, reaction mixture
  3. customwas returned to room temperature
  4. customSalts were removed by filtration, and acetonitrile
  5. distillationwas distilled off under reduced pressure
  6. additionWater was added to the residue
  7. extractionextracted with ethyl acetate
  8. washThe ethyl acetate layer was thoroughly washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off under reduced pressure
  11. distillationthe residue was subjected to distillation

Sources & evidence

ORD record
ord-7fe17686d8694b1d956633d542630f99
Source dataset
uspto-grants-1991_12
Patent number
US05076834

Reaction notes

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