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

HRID 358503Notes

Reaction equation

HRID 358503 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.C(OC(Cl)=O)C(C)C.[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.[Cl-].[Na+]>CN(C)C=O.C(N(CC)CC)C>[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

7

Reactant 4

HCID 5234Sodium ChlorideHCID 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 22.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8471TriethylamineSolvent

Procedure

To a solution of 4.8 g of 3,4-dimethoxybenzoic acid and 4 ml of triethylamine in 50 ml of dimethylformamide, a solution of 3.87 g of isobutylchloroformate in 2 ml of dimethylformamide was added dropwise. After the reaction mixture was stirred at a room temperature for 30 minutes, then a solution of 8.1 g of 6-(1-piperazinylcarbonyl)-3,4-dihydrocarbostyril in 3 ml of dimethylformamide was added dropwise to the reaction mixture and stirred at a room temperature for 30 minutes, and further stirred at 50°-60° C. for 1 hour. After the reaction was completed, the reaction mixture was poured into a voluminous amount of a saturated sodium chloride aqueous solution and then extracted with chloroform and the chloroform extract was washed with water and dried. The solvent was removed by distillation, and the residue was recrystallized from ethanol-chloroform to obtain 2.5 g of 6-[4-(3,4-dimethoxybenzoyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril. Colorless granular crystals. Melting point: 238°-239.5° C.

Workup

  1. stirringstirred at a room temperature for 30 minutes
  2. stirringfurther stirred at 50°-60° C. for 1 hour
  3. extractionextracted with chloroform
  4. extractionthe chloroform extract
  5. washwas washed with water
  6. customdried
  7. customThe solvent was removed by distillation
  8. customthe residue was recrystallized from ethanol-chloroform

Sources & evidence

ORD record
ord-7d422491e7714555afefa7e8a2ad763b
Source dataset
uspto-grants-1984_08
Patent number
US04468402

Reaction notes

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