Sodium Iodide → 6-{4-[2-(4-Chlorobenzoyl)ethyl]-1-piperazinylcarbonyl}-3,4-dihydrocarbostyril

HRID 477175Notes

Reaction equation

HRID 477175 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([CH2:8][CH2:9]Cl)=[O:7])=[CH:4][CH:3]=1.[I-].[Na+].[N:15]1([C:21]([C:23]2[CH:24]=[C:25]3[C:30](=[CH:31][CH:32]=2)[NH:29][C:28](=[O:33])[CH2:27][CH2:26]3)=[O:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([CH2:8][CH2:9][N:18]2[CH2:19][CH2:20][N:15]([C:21]([C:23]3[CH:24]=[C:25]4[C:30](=[CH:31][CH:32]=3)[NH:29][C:28](=[O:33])[CH2:27][CH2:26]4)=[O:22])[CH2:16][CH2:17]2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 775503,4'-DichloropropiophenoneHCID 131953426-(Piperazine-1-carbonyl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 140997836-{4-[2-(4-Chlorobenzoyl)ethyl]-1-piperazinylcarbonyl}-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

4.12 Grams of 2-(4-chlorobenzoyl)ethyl chloride and 6.08 g of sodium iodide were dispersed in 50 ml of dimethylformamide, and heated at 50° C. for 1.5 hours. Then, to this dispersion was added 50 ml of dimethylformamide solution containing 3 g of 6-(1-piperazinylcarbonyl)-3,4-dihydrocarbostyril, and further 9.8 g of potassium carbonate was added thereto and reacted by heating at 70° C. for 3 to 4 hours. After the reaction was completed, the insoluble matters were removed by filtration, and the solvent in the filtrate was removed by evaporation under reduced pressure. The residue thus obtained was extracted with chloroform, and the extract was dried with anhydrous calcium sulfate, then concentrated. The thus obtained residue was purified by means of a silica gel column chromatography (eluent: dichloromethane:methanol=50:1), then recrystallized from ethanol-diethyl ether to yield 2.29 g of 6-{4-[2-(4-chlorobenzoyl)ethyl]-1-piperazinylcarbonyl}-3,4-dihydrocarbostyril. White powdery substance.

Workup

  1. additionwas added
  2. customreacted
  3. temperatureby heating at 70° C. for 3 to 4 hours
  4. customthe insoluble matters were removed by filtration
  5. customthe solvent in the filtrate was removed by evaporation under reduced pressure
  6. customThe residue thus obtained
  7. extractionwas extracted with chloroform
  8. dry with materialthe extract was dried with anhydrous calcium sulfate
  9. concentrationconcentrated
  10. customThe thus obtained residue was purified by means of a silica gel column chromatography (eluent: dichloromethane:methanol=50:1)
  11. customrecrystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-eec5e12ef56644f5b8fb3831c152426d
Source dataset
uspto-grants-1989_12
Patent number
US04886809

Reaction notes

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