Hydrochloric Acid → HCID 15294649, compound

HRID 1734223Notes

Reaction equation

HRID 1734223 reaction equation
[Br:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:15]=[C:16]([CH:26]=[CH:27][CH:28]=3)[O:17][C:18]([CH3:25])([CH3:24])[C:19]([O:21]CC)=[O:20])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.O1CCOCC1.[OH-].[Na+].Cl>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:15]=[C:16]([CH:26]=[CH:27][CH:28]=3)[O:17][C:18]([CH3:25])([CH3:24])[C:19]([OH:21])=[O:20])[CH2:10][CH2:9]2)=[O:7])=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 15294648HCID 15294648, compound

Product 1

HCID 15294649HCID 15294649, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.90 g (4.00 mmol) of ethyl [3-{4-(4-bromobenzoyl)piperazinyl}phenoxy]α,α-dimethylacetate was dissolved in a solvent mixture containing 20 ml of dioxane and 20 ml of methanol, to which 20 ml of aqueous 1N NaOH solution was added and stirred for 2 hours at room temperature. After completion of the reaction, diluted hydrochloric acid was added to the reaction mixture to convert the system to acidic, followed by extraction with chloroform, washing with water and drying over anhydrous sodium sulfate. Subsequently, chloroform was distilled off under reduced pressure. The oily residue obtained was crystallized from a solvent mixture of petroleum ether, ether and ethyl acetate to obtain 1.45 g (81.0%) of the target compound as colorless crystals.

Workup

  1. additionwas added to the reaction mixture
  2. extractionfollowed by extraction with chloroform
  3. washwashing with water
  4. dry with materialdrying over anhydrous sodium sulfate
  5. distillationSubsequently, chloroform was distilled off under reduced pressure
  6. customThe oily residue obtained
  7. customwas crystallized from a solvent mixture of petroleum ether, ether and ethyl acetate

Sources & evidence

ORD record
ord-4de08d78a9fe4845acb7217776b791b0
Source dataset
uspto-grants-1996_07
Patent number
US05532371

Reaction notes

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