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

HRID 358501Notes

Reaction equation

HRID 358501 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.ClC(OCC(C)C)=O.[N:22]1([C:28]([C:30]2[CH:31]=[C:32]3[C:37](=[CH:38][CH:39]=2)[NH:36][C:35](=[O:40])[CH2:34][CH2:33]3)=[O:29])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>CN(C)C=O>[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:25]1[CH2:26][CH2:27][N:22]([C:28]([C:30]2[CH:31]=[C:32]3[C:37](=[CH:38][CH:39]=2)[NH:36][C:35](=[O:40])[CH2:34][CH2:33]3)=[O:29])[CH2:23][CH2:24]1)=[O:8]

Participants

5

Reactant 3

HCID 7121Veratric AcidHCID 62365Isobutyl chloroformateHCID 131953426-(Piperazine-1-carbonyl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 131953576-[4-(3,4-Dimethoxybenzoyl)-1-piperazinylcarbony]-3,4-dihydrocarbostyrilYield 42.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Into 100 ml of dimethylformamide, 2.6 g of 3,4-dimethoxybenzoic acid and 1.65 g of 1,8-diazabicyclo[5,4,0]undecene-7 were added, then the outside of the reaction vessel was ice-cooled and stirring condition, 1.5 ml of isobutyl chloroformate was added dropwise. Then the reaction mixture was further stirred for 30 minutes, a solution of 2.6 g of 6-(1-piperazinyl)carbonyl-3,4-dihydrocarbostyril dissolved in 40 ml of dimethylformamide was added to the reaction mixture and stirred at a room temperature for 5 hours. After the reaction was completed, the solvent was removed by distillation and the residue was extracted with about 300 ml of chloroform, then washed with a diluted sodium hydrogencarbonate aqueous solution, water, a diluted hydrochloric acid and water in this order. After removal of chloroform by distillation, the residue was recrystallized from ethanol-chloroform to obtain 1.8 g of 6-[4-(3,4-dimethoxybenzoyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril. Colorless granular crystals. Melting point: 238°-239.5° C.

Workup

  1. temperaturecooled
  2. additionwas added dropwise
  3. additionwas added to the reaction mixture
  4. stirringstirred at a room temperature for 5 hours
  5. customthe solvent was removed by distillation
  6. extractionthe residue was extracted with about 300 ml of chloroform
  7. washwashed with a diluted sodium hydrogencarbonate aqueous solution, water
  8. customAfter removal of chloroform
  9. distillationby distillation
  10. customthe residue was recrystallized from ethanol-chloroform

Sources & evidence

ORD record
ord-f2f1156e287842efa192d2c0fbc65f6d
Source dataset
uspto-grants-1984_08
Patent number
US04468402

Reaction notes

Loading…