Chloroacetic Acid → [4-(3,4-Dimethoxybenzoyl)-1-piperazinyl]-acetic acid

HRID 1381187Notes

Reaction equation

HRID 1381187 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7].[OH-].[K+].Cl[CH2:22][C:23]([OH:25])=[O:24]>CN(C)C=O.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH2:22][C:23]([OH:25])=[O:24])[CH2:12][CH2:13]1)=[O:7]

Participants

6

Reactant 3

HCID 300Chloroacetic AcidHCID 14797Potassium HydroxideHCID 8734071-(3,4-Dimethoxybenzoyl)piperazine

Product 1

HCID 20235788[4-(3,4-Dimethoxybenzoyl)-1-piperazinyl]-acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

32 Grams of 4-(3,4-dimethoxybenzoyl)piperazine and 13.1 g of potassium hydroxide were dissolved in 300 ml of dimethylformamide (DMF), then under an ice-cooled condition with stirring, 10 g of α-chloroacetic acid was added thereto, next the reaction mixture was heated at 50° C. for 5 hours with stirring. After completion of the reaction, the reaction mixture was concentrated to dryness, the residue obtained was dissolved in water. The solution obtained was washed with chloroform, the aqueous layer was neutralized with concentrated hydrochloric acid, crystals formed were collected by filtration to obtain 9.8 g of α-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetic acid.

Workup

  1. temperatureunder an ice-cooled condition
  2. stirringwith stirring
  3. customAfter completion of the reaction
  4. concentrationthe reaction mixture was concentrated to dryness
  5. customthe residue obtained
  6. customThe solution obtained
  7. washwas washed with chloroform
  8. customformed
  9. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-cb775512a34841e3a8513111fa5f2c5b
Source dataset
uspto-grants-1986_04
Patent number
US04585774

Reaction notes

Loading…