Ethanol → 3-{2-Amino-5-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]phenyl}-propionic acid

HRID 1649202

Reaction equation

HRID 1649202 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:7].C(O)C.[H][H]>[C].[Pd].O>[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:14][CH2:15][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)[CH2:17][CH2:18]2)=[CH:9][C:3]=1[CH2:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

6

Reactant 3

HCID 702EthanolHCID 542573532-Amino-5-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]cinnamic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 132363043-{2-Amino-5-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]phenyl}-propionic acidYield 29.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Procedure

2-Amino-5-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]cinnamic acid (5 g) was dissolved in a mixed solvent consisting of ethanol and water. After adding 5% palladium-carbon (0.5 g), the mixture was reduced at atmospheric pressure of hydrogen gas. After absorption of theoretical amount of hydrogen gas, the catalyst was removed by filtration and the ethanol-water phase was concentrated to dryness. The residue was dissolved in chloroform and separated through silica gel column chromatography to give 1.5 g of 3-{2-amino- 5-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]phenyl}-propionic acid, m.p. 98°-101° C.

Workup

  1. customAfter absorption of theoretical amount of hydrogen gas
  2. customthe catalyst was removed by filtration
  3. concentrationthe ethanol-water phase was concentrated to dryness
  4. dissolutionThe residue was dissolved in chloroform
  5. customseparated through silica gel column chromatography

Sources & evidence

ORD record
ord-c53a3f1c502f45449b0b607c4d6085a6
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Linked notes

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