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

HRID 1381197Notes

Reaction equation

HRID 1381197 reaction equation
[C:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[NH:6][C:7](=[O:10])[CH2:8][Cl:9])(=[O:3])[NH2:2].Cl.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[C:21]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)=[O:22].C(N(CC)CC)C>C(#N)C>[OH2:3].[ClH:9].[C:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[NH:6][C:7](=[O:10])[CH2:8][N:26]1[CH2:27][CH2:28][N:23]([C:21](=[O:22])[C:20]2[CH:29]=[CH:30][C:31]([O:32][CH3:33])=[C:18]([O:17][CH3:16])[CH:19]=2)[CH2:24][CH2:25]1)(=[O:3])[NH2:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5198892'-Carbamoyl-2-chloroacetanilideHCID 175176251-(3,4-Dimethoxybenzoyl)piperazine hydrochloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

5.00 Grams of o-carbamoyl-α-chloroacetanilide, 8.09 g of 3,4-dimethoxybenzoylpiperazine monohydrochloride, 8.31 g of triethylamine and 30 g of acetonitrile were mixed together and the mixture was stirred at 50° C. for 5 hours. Then the reaction mixture was ice-cooled, and the crystals formed were removed by filtration and the filtrate obtained was concentrated to dryness. The residue obtained was extracted with chloroform--1N sodium hydroxide aqueous solution, and 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 desired product was converted into a hydrochloride by using hydrochloric acid-ethanol, then recrystallized from water-acetone to obtain 7.43 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. temperaturecooled
  2. customthe crystals formed
  3. customwere removed by filtration
  4. customthe filtrate obtained
  5. concentrationwas concentrated to dryness
  6. customThe residue obtained
  7. extractionwas extracted with chloroform--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. customrecrystallized from water-acetone

Sources & evidence

ORD record
ord-f376dd2a73cb4c9ebc909044a52ccf6d
Source dataset
uspto-grants-1986_04
Patent number
US04585774

Reaction notes

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