Triethylamine → m-Methoxycarbonyl-alpha-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide

HRID 1381194Notes

Reaction equation

HRID 1381194 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10])=[O:4].Cl.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[C:22]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:23].C(N(CC)CC)C>C(#N)C>[CH3:12][O:11][C:9]([C:8]1[CH:7]=[C:6]([CH:15]=[CH:14][CH:13]=1)[NH:5][C:3](=[O:4])[CH2:2][N:27]1[CH2:28][CH2:29][N:24]([C:22](=[O:23])[C:21]2[CH:30]=[CH:31][C:32]([O:33][CH3:34])=[C:19]([O:18][CH3:17])[CH:20]=2)[CH2:25][CH2:26]1)=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2304955methyl 3-[(chloroacetyl)amino]benzoateHCID 175176251-(3,4-Dimethoxybenzoyl)piperazine hydrochloride

Product 1

HCID 13646256m-Methoxycarbonyl-alpha-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5 Grams of methyl m-(α-chloroacetylamino)benzoate, 7.56 g of N-(3,4-dimethoxybenzoyl)piperazine monohydrochloride, 7.76 g of triethylamine and 30 ml of acetonitrile were mixed together and reacted at 45° to 50° C. for 5 hours. After completion of the reaction, the reaction mixture was ice-cooled, and the crystals formed were removed by filtration. The mother liquor was concentrated to dryness, and extracted by adding 1 N-sodium hydroxide aqueous solution and chloroform. The chloroform layer was washed with water, dried and removed by distillation. The oily substance obtained was purified by a silica gel column chromatography to obtain 10.08 g of m-methoxycarbonyl-α-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide in the form of colorless oily substance.

Workup

  1. customreacted at 45° to 50° C. for 5 hours
  2. customAfter completion of the reaction
  3. temperaturecooled
  4. customthe crystals formed
  5. customwere removed by filtration
  6. concentrationThe mother liquor was concentrated to dryness
  7. extractionextracted
  8. additionby adding 1 N-sodium hydroxide aqueous solution and chloroform
  9. washThe chloroform layer was washed with water
  10. customdried
  11. customremoved by distillation
  12. customThe oily substance obtained
  13. customwas purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-02233a38139a4016aff92bdd247a9359
Source dataset
uspto-grants-1986_04
Patent number
US04585774

Reaction notes

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