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

HRID 1381201Notes

Reaction equation

HRID 1381201 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]([OH:17])=O)[CH2:10][CH2:9]1)=[O:7].[Cl:23]C(OCC(C)C)=O.[C:31]([C:34]1[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=1[NH2:36])(=[O:33])[NH2:32].Cl.Cl.C(O)C>CN(C=O)C.C(N(CC)CC)C>[OH2:2].[ClH:23].[C:31]([C:34]1[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=1[NH:36][C:15](=[O:17])[CH2:14][N:11]1[CH2:10][CH2:9][N:8]([C:6](=[O:7])[C:5]2[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:13][CH2:12]1)(=[O:33])[NH2:32]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6942AnthranilamideHCID 62365Isobutyl chloroformateHCID 20235788[4-(3,4-Dimethoxybenzoyl)-1-piperazinyl]-acetic acidHCID 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

2.77 Grams of [4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-acetic acid was dissolved in 30 ml of DMF, then to this solution was added 1.2 g of triethylamine. Under ice-cooled condition with stirring, 1.4 g of isobutyl chloroformate was added dropwise thereto and stirred for 30 minutes. Further, the reaction mixture was stirred at a room temperature, a DMF solution of 1.46 g of o-carbamoylaniline was added dropwise to the mixture and was stirred for 6 hours. The reaction mixture obtained was concentrated to dryness, the residue was extracted with chloroform and 1N-sodium hydroxide aqueous solution. The chloroform layer was washed with water, dried then chloroform was removed by distillation. The residue obtained was purified by a silica gel column chromatography and the product obtained was converted into a hydrochloride by adding hydrochloric acid-ethanol, then recrystallized from water-acetone to obtain 0.7 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. stirringstirred for 30 minutes
  3. stirringFurther, the reaction mixture was stirred at a room temperature
  4. stirringwas stirred for 6 hours
  5. customThe reaction mixture obtained
  6. concentrationwas concentrated to dryness
  7. extractionthe residue was extracted with chloroform and 1N-sodium hydroxide aqueous solution
  8. washThe chloroform layer was washed with water
  9. customdried
  10. customchloroform was removed by distillation
  11. customThe residue obtained
  12. customwas purified by a silica gel column chromatography
  13. customthe product obtained
  14. customrecrystallized from water-acetone

Sources & evidence

ORD record
ord-7167182f173e45939725fff74a63af34
Source dataset
uspto-grants-1986_04
Patent number
US04585774

Reaction notes

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