Piperazine → Caldaret

HRID 1603521Notes

Reaction equation

HRID 1603521 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 the Japanese Patent Unexamined Publication (KOKAI) No.(Hei)3-7263/1991, 2-fluoro-5-methylbenzenesulfonic acid (0.76 g) and piperazine (3.44 g) were reacted in a sealed tube in the presence of cuprous iodide (0.76 g) and copper powder (0.26 g) at 160° C. for 8 hours, and then the reaction product was purified by silica gel chromatography (eluent: chloroform: methanol: acetic acid=100:100:3) to give anhydrous crystals of 2-(1-piperazinyl)-5-methylbenzenesulfonic acid (0.67 g, yield: 65.0%).

Workup

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

Sources & evidence

ORD record
ord-243dfc28f2f94236a9da485da0318502
Source dataset
uspto-grants-1999_11
Patent number
US05990113

Reaction notes

Loading…