Sodium Iodide → 2(1H)-Quinolinone, 3,4-dihydro-6-(1-oxo-3-(4-phenyl-1-piperazinyl)propyl)-

HRID 1285428Notes

Reaction equation

HRID 1285428 reaction equation
[O:1]=[C:2]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]2)[CH2:3][CH2:4]Cl.[I-].[Na+].[C:19]1([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])O.[Na+]>C(O)(C)C>[O:1]=[C:2]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]2)[CH2:3][CH2:4][N:28]1[CH2:29][CH2:30][N:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:26][CH2:27]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 70961-PhenylpiperazineHCID 516892Sodium BicarbonateHCID 12833509HCID 12833509, compound

Product 1

HCID 30670732(1H)-Quinolinone, 3,4-dihydro-6-(1-oxo-3-(4-phenyl-1-piperazinyl)propyl)-

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2.4 Grams of 6-(1-oxo-3-chloropropyl)-3,4-dihydrocarbostyril and 1.6 g of sodium iodide were mixed with 60 ml of isopropanol and the mixture was stirred at 40°-50° C. for 2 hours. Then to this reaction mixture were added 2.0 g of 4-phenylpiperazine and 3.0 g of DBU (1,5-diazabicyclko[5,4,0]undecane-5) and refluxed by heating for 6 hours. Then the reaction mixture was poured into 100 ml of 5%-sodium hydrogen-carbonate solution and stirred at a room temperature foir 1 hour. The insoluble matters were collected by filtration, washed with water and dried, then recrystallized from ethanol-chloroform to obtain 1.9 g of 6-[1-oxo-3-(4-phenylpiperazinyl)-propyl]-3,4-dihydrocarbostyril in colorless flake-like crystals.

Workup

  1. temperaturerefluxed
  2. temperatureby heating for 6 hours
  3. stirringstirred at a room temperature foir 1 hour
  4. filtrationThe insoluble matters were collected by filtration
  5. washwashed with water
  6. customdried
  7. customrecrystallized from ethanol-chloroform

Sources & evidence

ORD record
ord-8000695e20ed45ce98f44266d372ca56
Source dataset
uspto-grants-1986_01
Patent number
US04567187

Reaction notes

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