Dicyclohexylcarbodiimide → 6-(4-Benzyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyril

HRID 358496Notes

Reaction equation

HRID 358496 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]2)([OH:3])=O.C1CCC(N=C=NC2CCCCC2)CC1.[CH2:30]([N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCOCC1>[CH2:30]([N:37]1[CH2:42][CH2:41][N:40]([C:1]([C:4]2[CH:5]=[C:6]3[C:11](=[CH:12][CH:13]=2)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]3)=[O:3])[CH2:39][CH2:38]1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 759941-BenzylpiperazineHCID 71319092-Oxo-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

Product 1

HCID 131953356-(4-Benzyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

1.0 Gram of 6-carboxy-3,4-dihydrocarbostyril, 1.3 g of DCC and 1.1 g of benzylpiperazine were suspended in 10 ml of dioxane and the suspension was stirred at 70° C. for 5 hours. After the reaction was completed, the solvent was removed by distillation and ether was added to the residue and crystals formed were removed by filtration. After the mother liquor was concentrated, the residue was dissolved in chloroform and the chloroform solution was washed with water and a saturated sodium chloride aqueous solution then dried with anhydrous sodium sulfate and the solvent was removed by distillation. Recrystallized from ethanol to obtain 330 mg of 6-(4-benzyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyril. Colorless needle-like crystals. Melting point: 198°-200° C.

Workup

  1. customthe solvent was removed by distillation and ether
  2. additionwas added to the residue and crystals
  3. customformed
  4. customwere removed by filtration
  5. concentrationAfter the mother liquor was concentrated
  6. dissolutionthe residue was dissolved in chloroform
  7. washthe chloroform solution was washed with water
  8. dry with materiala saturated sodium chloride aqueous solution then dried with anhydrous sodium sulfate
  9. customthe solvent was removed by distillation
  10. customRecrystallized from ethanol

Sources & evidence

ORD record
ord-3f6823880bed456297b484031d145bf8
Source dataset
uspto-grants-1984_08
Patent number
US04468402

Reaction notes

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