2-Amino-5-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]cinnamic acid → Vesnarinone

HRID 1649251

Reaction equation

HRID 1649251 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][N:16]([C:19](=[O:30])[C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=3)[CH2:15][CH2:14]2)=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=O.[H][H]>CN(C=O)C.[C].[Pd]>[CH3:29][O:28][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][C:23]=1[O:26][CH3:27])[C:19]([N:16]1[CH2:15][CH2:14][N:13]([C:10]2[CH:9]=[C:3]3[C:2](=[CH:12][CH:11]=2)[NH:1][C:6](=[O:8])[CH2:5][CH2:4]3)[CH2:18][CH2:17]1)=[O:30]

Participants

5

Reactant 2

HCID 542573532-Amino-5-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]cinnamic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 5663VesnarinoneYield 60.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

2-Amino-5-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]cinnamic acid (5 g) was dissolved in DMF (50 ml), and 5% palladium-carbon (0.5 g) was added to the solution. The mixture was reacted at 80° C. for 4 hours using Parr's apparatus at a hydrogen gas pressure of 3 kg/cm2. After removing hydrogen gas, the content was taken out. After removing the catalyst, the reaction mixture was concentrated to half the original volume and poured into a large volume of water. Crystals which precipitated were collected by filtration and recrystallized from ethanol-chloroform to give 2.9 g of 6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril, m.p. 238°-239.5° C., colorless granules.

Workup

  1. customThe mixture was reacted at 80° C. for 4 hours
  2. customAfter removing hydrogen gas
  3. customAfter removing the catalyst
  4. concentrationthe reaction mixture was concentrated to half the original volume
  5. additionpoured into a large volume of water
  6. customCrystals which precipitated
  7. filtrationwere collected by filtration
  8. customrecrystallized from ethanol-chloroform

Sources & evidence

ORD record
ord-bf0212f2c8444c8898615ac55ebd1cb8
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Linked notes

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