Hydrochloric Acid → o-Carboxy--[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide monohydrochloride

HRID 1381202Notes

Reaction equation

HRID 1381202 reaction equation
C[O:2][C:3]([C:5]1[CH:32]=[CH:31][CH:30]=[CH:29][C:6]=1[NH:7][C:8](=[O:28])[CH2:9][N:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:27])[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=2)[CH2:12][CH2:11]1)=[O:4].CO.CO.[OH-].[K+].[ClH:39]>C(O)C>[ClH:39].[C:3]([C:5]1[CH:32]=[CH:31][CH:30]=[CH:29][C:6]=1[NH:7][C:8](=[O:28])[CH2:9][N:10]1[CH2:11][CH2:12][N:13]([C:16](=[O:27])[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=2)[CH2:14][CH2:15]1)([OH:4])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 13117363o-Methoxycarbonyl--[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilideHCID 23689386Potassium hydroxide methanol

Product 1

HCID 23323535o-Carboxy--[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide monohydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20 Grams of o-methoxycarbonyl- -[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide, 400 ml of methanol and 25 ml of 3.5N-potassium hydroxide methanol solution were mixed together and the mixture was refluxed for 8.5 hours. After completion of the reaction, the reaction mixture was allowed to stand for cooling, then an ethanol solution of hydrochloric acid was added to the mixture to adjust the pH thereof to about 1. The crystals formed were removed by filtration, and the mother liquor was cooled by ice. The crystals were collected by filtration, recrystallized from 80% water-containing methanol to obtain 13.28 g of o-carboxy- -[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide monohydrochloride in the form of colorless cotton fiber-like crystals. Melting point: 250.5°-251.5° C. (decomposed).

Workup

  1. temperaturethe mixture was refluxed for 8.5 hours
  2. customAfter completion of the reaction
  3. temperaturefor cooling
  4. customThe crystals formed
  5. customwere removed by filtration
  6. temperaturethe mother liquor was cooled by ice
  7. filtrationThe crystals were collected by filtration
  8. customrecrystallized from 80% water-
  9. additioncontaining methanol

Sources & evidence

ORD record
ord-50fe267d546d4303a5f4e55d8ef24b8b
Source dataset
uspto-grants-1986_04
Patent number
US04585774

Reaction notes

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