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

HRID 1262852Notes

Reaction equation

HRID 1262852 reaction equation
C(O)C.C(O[C:7]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=[O:19])[CH2:13][CH2:12]2)=[O:8])C.CC[O-].[Na+].[CH2:24]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)(Cl)Cl>[CH2:24]([N:31]1[CH2:36][CH2:35][N:34]([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])[CH2:33][CH2:32]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 759941-BenzylpiperazineHCID 2723922Sodium ethoxideHCID 14497706Ethyl 2-oxo-1,2,3,4-tetrahydroquinoline-6-carboxylate

Product 1

HCID 131953356-(4-Benzyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyrilYield 9.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 100 ml of ethanol was added 2.0 g of 6-ethoxycarbonyl-3,4-dihydrocarbostyril, 0.5 g of sodium ethylate and 1.6 g of benzylpiperazine, the mixture was reacted in an autoclave under 110 atmospheric pressure at 140°-150° C. for 6 hours. After the reaction was completed, the reaction mixture was cooled and concentrated under a reduced pressure. The residue thus obtained was dissolved in 200 ml of chloroform and the chloroform solution was washed with 1%-potassium carbonate aqueous solution, a diluted hydrochloric acid and water in this order, then dried with anhydrous sodium sulfate. The solvent was removed by distillation and the residue was treated by means of a silica gel column chromatography (Silica gel: Wako C-200, eluate: chloroform:methanol (volume/volume)=20:1) and the crude crystals were recrystallized from ethanol to obtain 300 mg of 6-(4-benzyl-1-piperazinylcarbonyl)-3,4-dihyrocarbostyril. Colorless needle-like crystals. Melting point: 198°-200° C.

Workup

  1. customthe mixture was reacted in an autoclave under 110 atmospheric pressure at 140°-150° C. for 6 hours
  2. temperaturethe reaction mixture was cooled
  3. concentrationconcentrated under a reduced pressure
  4. customThe residue thus obtained
  5. washthe chloroform solution was washed with 1%-potassium carbonate aqueous solution
  6. dry with materiala diluted hydrochloric acid and water in this order, then dried with anhydrous sodium sulfate
  7. customThe solvent was removed by distillation
  8. additionthe residue was treated by means of a silica gel column chromatography (Silica gel: Wako C-200, eluate: chloroform:methanol (volume/volume)=20:1)
  9. customthe crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-ce231d72caa34dad8ae7f7a1c1c0c9af
Source dataset
uspto-grants-1984_06
Patent number
US04454130

Reaction notes

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