Water → 6-{1-Oxo-2-[4-(4-nitrophenyl)-1-piperazinyl]-butyl}-3,4-dihydrocarbostyril

HRID 1263123Notes

Reaction equation

HRID 1263123 reaction equation
[O:1]=[C:2]([C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])[CH2:16][CH2:15]2)[CH:3]([N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)[CH2:4][CH3:5].Br[C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].O>CCOCCO.[Cu]>[O:1]=[C:2]([C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])[CH2:16][CH2:15]2)[CH:3]([N:6]1[CH2:11][CH2:10][N:9]([C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[CH2:8][CH2:7]1)[CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 114661-Bromo-4-nitrobenzeneHCID 572943156-(1-Oxo-2-piperazinylbutyl)-3,4-dihydrocarbostyril

Product 1

HCID 130648616-{1-Oxo-2-[4-(4-nitrophenyl)-1-piperazinyl]-butyl}-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8076Glycol monoethyl etherSolvent

Procedure

1.8 Grams of 6-(1-oxo-2-piperazinylbutyl)-3,4-dihydrocarbostyril, 2.0 g of p-bromonitrobenzene, 1.2 g of potassium carbonate and 0.1 g of copper powder were dispersed in 80 ml of ethyl cellosolve and stirred at 120°-150° C. by heating for 5 hours. The reaction mixture was concentrated under a reduced pressure and the residue thus obtained was added water and extracted with chloroform. The chloroform layer was washed with water, dried and the chloroform was removed by distillation. The residue thus obtained was separated and purified by a separative thin layer chromatography and recrystallized from ethanol to obtain 0.2 g of 6-{1-oxo-2-[4-(4-nitrophenyl)-1-piperazinyl]-butyl}-3,4-dihydrocarbostyril in yellow powdery crystals.

Workup

  1. temperatureby heating for 5 hours
  2. concentrationThe reaction mixture was concentrated under a reduced pressure
  3. customthe residue thus obtained
  4. extractionextracted with chloroform
  5. washThe chloroform layer was washed with water
  6. customdried
  7. customthe chloroform was removed by distillation
  8. customThe residue thus obtained
  9. customwas separated
  10. custompurified by a separative thin layer chromatography
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-ba185d5b147646969219964d50c99f68
Source dataset
uspto-grants-1984_06
Patent number
US04455422

Reaction notes

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