Ethanol → 6-[4-(3,4-Dimethoxybenzoyl)-1-piperazinylcarbony]-3,4-dihydrocarbostyril

HRID 1262856Notes

Reaction equation

HRID 1262856 reaction equation
C(O)C.[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:9]([O:11]CC)=O.CC[O-].[Na+].[N:23]1([C:29]([C:31]2[CH:32]=[C:33]3[C:38](=[CH:39][CH:40]=2)[NH:37][C:36](=[O:41])[CH2:35][CH2:34]3)=[O:30])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>C(Cl)(Cl)Cl>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:9]([N:26]1[CH2:27][CH2:28][N:23]([C:29]([C:31]2[CH:32]=[C:33]3[C:38](=[CH:39][CH:40]=2)[NH:37][C:36](=[O:41])[CH2:35][CH2:34]3)=[O:30])[CH2:24][CH2:25]1)=[O:11]

Participants

6

Reactant 4

HCID 702EthanolHCID 77546Benzoic acid, 3,4-dimethoxy-, ethyl esterHCID 2723922Sodium ethoxideHCID 131953426-(Piperazine-1-carbonyl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 131953576-[4-(3,4-Dimethoxybenzoyl)-1-piperazinylcarbony]-3,4-dihydrocarbostyrilYield 6.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 100 ml of ethanol was added 1.9 g of ethyl 3,4-dimethoxybenzoate, 0.5 g sodium ethylate and 2.4 g of 6-(1-piperazinylcarbonyl)-3,4-dihydrocarbostyril, 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 dilute 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, eluent: chloroform:methanol (volume/volume)=20:1) and the crude crystals were recrystallized from ethanol-chloroform to obtain 250 mg of 6-[4-(3,4-dimethoxybenzoyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril. Colorless granular crystals. Melting point: 238°-239.5° 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 dilute 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, eluent: chloroform:methanol (volume/volume)=20:1)
  9. customthe crude crystals were recrystallized from ethanol-chloroform

Sources & evidence

ORD record
ord-e0da9f5d31e94b9f8377ceac2fff35e6
Source dataset
uspto-grants-1984_06
Patent number
US04454130

Reaction notes

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