Piperazine → Caldaret

HRID 344661Notes

Reaction equation

HRID 344661 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[S:9]([OH:12])(=[O:11])=[O:10].[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>[Cu](I)I.[Cu]>[N:13]1([C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=2[S:9]([OH:12])(=[O:11])=[O:10])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 4837PiperazineHCID 149947842-Fluoro-5-methylbenzene-1-sulfonic acid

Product 1

HCID 6433076CaldaretYield 65.4%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 83717Copper iodideCatalyst

Procedure

After the reaction was carried out between 0.76 g of 2-fluoro-5-methylbenzenesulfonic acid and 3.44 g of piperazine in the co-presence of 0.76 g of copper iodide and 0.26 g of copper powder in a sealed tube at 160° C. for 8 hours, the reaction product was purified by silica gel column chromatography (eluant:chloroform:methanol:acetic acid =100:100:3) to give 0.67 g (yield: 65.0%) of the above title product having the following physical property.

Workup

  1. customthe reaction product was purified by silica gel column chromatography (eluant:chloroform:methanol:acetic acid =100:100:3)

Sources & evidence

ORD record
ord-475f7637557c4ed0bf9c9fa65532acab
Source dataset
uspto-grants-1991_10
Patent number
US05053409

Reaction notes

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