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

HRID 358493Notes

Reaction equation

HRID 358493 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.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[C:25](Cl)=[O:26].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[C:25]([N:4]1[CH2:5][CH2:6][N: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])[CH2:2][CH2:3]1)=[O:26]

Participants

5

Reactant 3

HCID 77070Veratroyl chlorideHCID 516892Sodium BicarbonateHCID 131953426-(Piperazine-1-carbonyl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 131953576-[4-(3,4-Dimethoxybenzoyl)-1-piperazinylcarbony]-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.0 Grams of 6-(1-piperazinylcarbonyl)-3,4-dihydrocarbostyril and 4.0 ml of tiethylamine were suspended in 20 ml of dichloromethane, and to the suspension was added dropwise 3.5 g of 3,4-dimethoxybenzoylchloride in 20 ml of dichloromethane under ice-cooled condition with stirring. Then the reaction was continued for additional 1 hour at a room temperature. The reaction mixture was poured into a saturated sodium bicarbonate aqueous solution and extracted with chloroform. The chloroform layer was washed with water and a saturated sodium chloride aqueous solution in this order and was dried with anhydrous sodium sulfate, and the solvent was removed by distillation. The residue thus obtained was recrystallized from ethanol-chloroform to obtain 4.1 g of 6-[4-(3,4-dimethoxybenzoyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril. Colorless granular crystals. Melting point: 238°-239.5° C.

Workup

  1. temperaturecooled condition
  2. extractionextracted with chloroform
  3. washThe chloroform layer was washed with water
  4. dry with materiala saturated sodium chloride aqueous solution in this order and was dried with anhydrous sodium sulfate
  5. customthe solvent was removed by distillation
  6. customThe residue thus obtained
  7. customwas recrystallized from ethanol-chloroform

Sources & evidence

ORD record
ord-e480fa4f82ff4524b03f042013c86c0a
Source dataset
uspto-grants-1984_08
Patent number
US04468402

Reaction notes

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