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

HRID 358505Notes

Reaction equation

HRID 358505 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.[N:14]1([C:20]([C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[NH:28][C:27](=[O:32])[CH2:26][CH2:25]3)=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.O1CCOCC1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([N:17]1[CH2:18][CH2:19][N:14]([C:20]([C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[NH:28][C:27](=[O:32])[CH2:26][CH2:25]3)=[O:21])[CH2:15][CH2:16]1)=[O:8]

Participants

5

Reactant 3

HCID 7121Veratric AcidHCID 312751,4-DioxaneHCID 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 6344DichloromethaneSolvent3×

Procedure

1.8 Grams of 3,4-dimethoxybenzoic acid and 2.75 g of 6-(1-piperazinylcarbonyl)-3,4-dihydrocarbostyril were added to a mixed solvent of 20 ml of dioxane with 20 ml of methylene chloride. Under the condition that the outside of reaction vessel was ince-cooled with stirring, a solution of 2.1 g of N,N-dicyclohexylcarbodiimide being dissolved in 5 ml of methylene chloride by keeping its temperature to 10°-20° C. was added dropwise thereto and stirred at the same temperature for 3.5 hours. The crystals formed in the reaction mixture were removed by filtration, and the mother liquor was concentrated under a reduced pressure. The residue thus obtained was dissolved in 100 ml of methylene chloride and the organic layer was washed with 5%-hydrochloric acid aqueous solution, 5%-sodium hydrogen-carbonate aqueous solution and water in this order, then the organic layer was dried with anhydrous sodium sulfate. The solvent was removed by distillation under a reduced pressure and the residue thus obtained was recrystallized from chloroform-ethanol to obtain 0.9 g of 6-[4-(3,4-dimethoxybenzoyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril. Colorless granular crystals. Melting point: 238°-239.5° C.

Workup

  1. customUnder the condition that the outside of reaction vessel
  2. temperaturewas ince-cooled
  3. customto 10°-20° C.
  4. additionwas added dropwise
  5. stirringstirred at the same temperature for 3.5 hours
  6. customThe crystals formed in the reaction mixture
  7. customwere removed by filtration
  8. concentrationthe mother liquor was concentrated under a reduced pressure
  9. customThe residue thus obtained
  10. washthe organic layer was washed with 5%-hydrochloric acid aqueous solution, 5%-sodium hydrogen-carbonate aqueous solution and water in this order
  11. dry with materialthe organic layer was dried with anhydrous sodium sulfate
  12. customThe solvent was removed by distillation under a reduced pressure
  13. customthe residue thus obtained
  14. customwas recrystallized from chloroform-ethanol

Sources & evidence

ORD record
ord-b44a62a9a0254694b5a05affae41ea15
Source dataset
uspto-grants-1984_08
Patent number
US04468402

Reaction notes

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