1-Phenylpiperazine → 2(1H)-Quinolinone, 3,4-dihydro-1-methyl-6-(1-oxo-3-(4-phenyl-1-piperazinyl)propyl)-, ethanedioate (1:1)

HRID 1285432Notes

Reaction equation

HRID 1285432 reaction equation
[CH3:1][N:2]1[C:12]2[C:7](=[CH:8][C:9]([C:13](=[O:17])[CH2:14][CH2:15]Cl)=[CH:10][CH:11]=2)[CH2:6][CH2:5][C:3]1=[O:4].[C:18]1([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])O.[Na+].CC(C)=O.[C:39]([OH:44])(=[O:43])[C:40]([OH:42])=[O:41]>CC(C)=O.CN(C)C=O.N1C=CC=CC=1>[C:39]([OH:44])(=[O:43])[C:40]([OH:42])=[O:41].[CH3:1][N:2]1[C:12]2[C:7](=[CH:8][C:9]([C:13](=[O:17])[CH2:14][CH2:15][N:27]3[CH2:28][CH2:29][N:24]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH2:25][CH2:26]3)=[CH:10][CH:11]=2)[CH2:6][CH2:5][C:3]1=[O:4]

Participants

8

Reactant 4

HCID 70961-PhenylpiperazineHCID 516892Sodium BicarbonateHCID 128335081-Methyl-6-(1-oxo-3-chloropropyl)-3,4-dihydrocarbostyrilHCID 88629647Oxalic acid acetone

Product 1

HCID 30671782(1H)-Quinolinone, 3,4-dihydro-1-methyl-6-(1-oxo-3-(4-phenyl-1-piperazinyl)propyl)-, ethanedioate (1:1)

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

2.6 Grams of 1-methyl-6-(1-oxo-3-chloropropyl)-3,4-dihydrocarbostyril, 1.2 g of pyridine and 2.0 g of 4-phenylpiperazine were mixed into 30 ml of dimethylformamide and the mixture was stirred at 70°-80° C. for 7 hours. The reaction mixture was poured into 100 ml of 5%-sodium hydrogencarbonate solution and was extracted with chloroform. The chloroform layer was washed with water, dried and chloroform was removed by distillation. The residue thus obtained was dissolved with acetone and the pH of the solution was adjusted to pH 4 by adding 5%-oxalic acid acetone solution to form crystalline precipitates. The precipitates were collected by filtration and recrystallized from ethanol-water to obtain 2.8 g of 1-methyl-6-[1-oxo-3-(4-phenyl-1-piperazinyl)propyl]-3,4-dihydrocarbostyril monooxalate in colorless flake-like crystals.

Workup

  1. extractionwas extracted with chloroform
  2. washThe chloroform layer was washed with water
  3. customdried
  4. customchloroform was removed by distillation
  5. customThe residue thus obtained
  6. customto form crystalline precipitates
  7. filtrationThe precipitates were collected by filtration
  8. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-5cc968bfefa1479982a1b27a535a2448
Source dataset
uspto-grants-1986_01
Patent number
US04567187

Reaction notes

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