Piperazine → Caldaret

HRID 2186723Notes

Reaction equation

HRID 2186723 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]>[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

4

Reactant 2

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

Product 1

HCID 6433076CaldaretYield 65.4%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

According to the method described in Example 1 of Japanese Patent Application Laid-Open No. 3-7263, 2-fluoro-5-methylbenzene sulfonic acid (0.76 g) was reacted with piperazine (3.44 g) in the co-presence of cuprous iodide (0.76 g) and copper powder (0.26 g) in a sealed tube at 160° C. for 8 hours. Then, the reaction product was purified on silica gel column chromatography (eluent=chloroform: methanol: acetic acid=100: 100: 3) to give anhydrous crystal of 2-(1-piperazinyl)-5-methylbenzenesulfonic acid derivative (0.67 g, yield=65.0%).

Workup

  1. customThen, the reaction product was purified on silica gel column chromatography (eluent=chloroform: methanol: acetic acid=100: 100: 3)

Sources & evidence

ORD record
ord-594688991b3f42fdb69101555d320339
Source dataset
uspto-grants-2002_06
Patent number
US06407113B1

Reaction notes

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