4-Toluenesulfonyl chloride → 6-[4-(p-Toluenesulfonyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril

HRID 358494Notes

Reaction equation

HRID 358494 reaction equation
[N:1]1([C:7]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH2:13][CH2:12]3)=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>ClCCl>[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([C:9]3[CH:10]=[C:11]4[C:16](=[CH:17][CH:18]=3)[NH:15][C:14](=[O:19])[CH2:13][CH2:12]4)=[O:8])[CH2:2][CH2:3]2)(=[O:35])=[O:34])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 131953426-(Piperazine-1-carbonyl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 131953666-[4-(p-Toluenesulfonyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.5 Grams of 6-(1-piperazinylcarbonyl)-3,4-dihydrocarbostyril and 1.5 g of triethylamine were suspended in 10 ml of dichloromethane. Under ice-cooled and stirring condition, 1.4 g of p-toluenesulfonylchloride in 10 ml of dichloromethane solution was added dropwise to the suspension and the reaction was continued for additionally 3 hours at a room temperature, further continued for 1 hour under ice-cooled condition. The crystals formed in the reaction mixture were collected by filtration and recrystallized from chloroform-ether to obtain 1.4 g of 6-[4-(p-toluenesulfonyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril. Colorless granular crystals. Melting point: 280°-282° C.

Workup

  1. temperatureUnder ice-cooled
  2. additionwas added dropwise to the suspension
  3. waitfurther continued for 1 hour under ice-
  4. temperaturecooled condition
  5. customThe crystals formed in the reaction mixture
  6. filtrationwere collected by filtration
  7. customrecrystallized from chloroform-ether

Sources & evidence

ORD record
ord-828e4c3d378e4919a6205e3dab58e3f6
Source dataset
uspto-grants-1984_08
Patent number
US04468402

Reaction notes

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