1-{[5-(1-Hydroxyethyl)-2-methoxy-4-methylphenyl]aminocarbonyl}-4-(3,5-dimethoxyphenyl)piperazine → 1-[(2-Methoxy-4-methyl-5-vinylphenyl)aminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazine

HRID 377931Notes

Reaction equation

HRID 377931 reaction equation
O[CH:2]([C:4]1[C:5]([CH3:31])=[CH:6][C:7]([O:29][CH3:30])=[C:8]([NH:10][C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[CH:9]=1)[CH3:3].C1C=CC(N=NC2C=CC(N)=NC=2N)=CC=1.Cl.CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[CH3:30][O:29][C:7]1[CH:6]=[C:5]([CH3:31])[C:4]([CH:2]=[CH2:3])=[CH:9][C:8]=1[NH:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:20]=[C:21]([O:27][CH3:28])[CH:22]=[C:23]([O:25][CH3:26])[CH:24]=2)[CH2:15][CH2:14]1)=[O:12]

Participants

4

Reactant 2

HCID 193570541-{[5-(1-Hydroxyethyl)-2-methoxy-4-methylphenyl]aminocarbonyl}-4-(3,5-dimethoxyphenyl)piperazineHCID 21909214Pyridium p-toluenesulfonate

Product 1

HCID 193569531-[(2-Methoxy-4-methyl-5-vinylphenyl)aminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazineYield 84%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-{[5-(1-Hydroxyethyl)-2-methoxy-4-methylphenyl]aminocarbonyl}-4-(3,5-dimethoxyphenyl)piperazine(0.2 g, 0.47 mmol) was dissolved in chloroform(15 ml), pyridium p-toluenesulfonate(0.12 g, 0.47 mmol) was added thereto, and the resulting mixture was refluxed for 16 hours, and concentrated under the reduced pressure to remove chloroform and purified by column chromatography(ethylacetate:hexane=1:2) to obtain the titled compound.

Workup

  1. temperaturethe resulting mixture was refluxed for 16 hours
  2. concentrationconcentrated under the reduced pressure
  3. customto remove chloroform
  4. custompurified by column chromatography(ethylacetate:hexane=1:2)

Sources & evidence

ORD record
ord-1ea6c7328c8a40bab6d6807561d9ca1d
Source dataset
uspto-grants-2000_02
Patent number
US06028195

Reaction notes

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