Potassium Hydroxide → HCID 15754177, compound

HRID 1461661Notes

Reaction equation

HRID 1461661 reaction equation
[CH3:1][C:2]([N:10]([CH2:20][CH2:21][C:22](=O)[CH3:23])[C:11](=[O:19])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[K+]>C(O)C>[CH3:1][C:2]([N:10]1[CH2:20][CH2:21][C:22]([CH3:23])=[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:11]1=[O:19])([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 15754162HCID 15754162, compound

Product 1

HCID 15754177HCID 15754177, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7.1 g (0.022 mol) of N-(α,α-dimethylbenzyl)-N-(3-oxobutyl)phenylacetamide prepared by the method of Reference Example 10, was dissolved in 50 ml of ethanol, and 0.33 g (0.005 mol) of potassium hydroxide powder was added thereto. The mixture was reflux under heating for 1.5 hours. Then, the reaction mixture was returned to room temperature, and ethanol was distilled off under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. Then ethyl acetate layer was washed with water and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue thereby obtained was recrystallized from ethanol to obtain 4.5 g (yield: 67.2%) of the desired compound.

Workup

  1. temperatureThe mixture was reflux
  2. temperatureunder heating for 1.5 hours
  3. customwas returned to room temperature
  4. distillationethanol was distilled off under reduced pressure
  5. additionWater was added to the residue
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThen ethyl acetate layer was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customThe residue thereby obtained
  11. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-26cedef2da924023a2b7e0fd9a49108c
Source dataset
uspto-grants-1991_12
Patent number
US05076834

Reaction notes

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