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

HRID 1381199Notes

Reaction equation

HRID 1381199 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.[Cl:14]C(OCC(C)C)=O.[C:22]([C:25]1[CH:40]=[CH:39][CH:38]=[CH:37][C:26]=1[NH:27][C:28](=[O:36])[CH2:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)(=[O:24])[NH2:23].Cl.Cl.C(O)C>CN(C)C=O.C(N(CC)CC)C>[OH2:2].[ClH:14].[C:22]([C:25]1[CH:40]=[CH:39][CH:38]=[CH:37][C:26]=1[NH:27][C:28](=[O:36])[CH2:29][N:30]1[CH2:35][CH2:34][N:33]([C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:32][CH2:31]1)(=[O:24])[NH2:23]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7121Veratric AcidHCID 62365Isobutyl chloroformateHCID 13646249o-Carbamoyl-alpha-(1-piperazinyl)acetanilideHCID 21887872Ethanol hydrochloride

Product 1

HCID 23323531o-Carbamoyl-alpha-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide monohydrochloride monohydrate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

3.3 Grams of 3,4-dimethoxybenzoic acid was dissolved in 30 ml of dimethylformamide, and to this solution was added 2.4 g of triethylamine. Under ice-cooled condition with stirring, 2.75 g of isobutyl chloroformate was added dropwise and the mixture obtained was stirred for 30 minutes. To this reaction mixture was added dropwise a dimethylformamide solution of 5.5 g of o-carbamoyl-α-(1-piperazinyl)acetanilide and was stirred for 5 hours. The reaction mixture was concentrated to dryness and extracted with chloroform-1N sodium hydroxide aqueous solution. The chloroform layer was washed with water, dried and chloroform was removed by distillation, the residue thus obtained was purified by a silica gel column chromatography and the product obtained was converted into a hydrochloride by adding hydrochloric acid-ethanol, recrystallized from water-acetone to obtain 1.5 g of o-carbamoyl-α-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide monohydrochloride monohydrate in the form of colorless needle-like crystals. Melting point: 122.0°-125.0° C. (decomposed).

Workup

  1. temperatureUnder ice-cooled condition
  2. customthe mixture obtained
  3. stirringwas stirred for 30 minutes
  4. stirringwas stirred for 5 hours
  5. concentrationThe reaction mixture was concentrated to dryness
  6. extractionextracted with chloroform-1N sodium hydroxide aqueous solution
  7. washThe chloroform layer was washed with water
  8. customdried
  9. customchloroform was removed by distillation
  10. customthe residue thus obtained
  11. customwas purified by a silica gel column chromatography
  12. customthe product obtained
  13. customrecrystallized from water-acetone

Sources & evidence

ORD record
ord-1183a534ebee406bb25e10211d822581
Source dataset
uspto-grants-1986_04
Patent number
US04585774

Reaction notes

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