Phenylacetyl chloride → HCID 15754166, compound

HRID 1461669Notes

Reaction equation

HRID 1461669 reaction equation
[CH3:1][C:2]([NH:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[C:24]1([CH2:30][C:31](Cl)=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CC(C)=O>[C:24]1([CH2:30][C:31]([N:10]([C:2]([CH3:1])([CH3:9])[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 11430Potassium CarbonateHCID 15754165HCID 15754165, compound

Product 1

HCID 15754166HCID 15754166, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

47.0 g (0.2 mol) of ethyl 3-(α,α-dimethylbenzylamino)propionate prepared by the method of Reference Example 16, was dissolved in 200 ml of acetone, and 30 g (0.22 mol) of potassium carbonate was added thereto. 31.0 g (0.2 mol) phenyl acetic acid chloride was dropwise added thereto at room temperature. After completion of the dropwise addition, the reaction solution was stirred for one day and night, and the reaction solvent was distilled off under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate, washed with water and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 63.0 g (yield: 89.1%) of the desired compound.

Workup

  1. customat room temperature
  2. additionAfter completion of the dropwise addition
  3. distillationthe reaction solvent was distilled off under reduced pressure
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-70adcef099194c2e9491996457cf1e5f
Source dataset
uspto-grants-1991_12
Patent number
US05076834

Reaction notes

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