Piperazine → N,N'-bis[[2-(3,4,5-Trimethoxyphenyl)thiazol-4-yl]methyl]piperazine

HRID 992987Notes

Reaction equation

HRID 992987 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=2)[S:6][CH:7]=1.[NH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.[C:26](=[O:29])([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[CH3:19][O:18][C:10]1[CH:9]=[C:8]([C:5]2[S:6][CH:7]=[C:3]([CH2:2][N:20]3[CH2:25][CH2:24][N:23]([CH2:2][C:3]4[N:4]=[C:5]([C:8]5[CH:9]=[C:10]([O:18][CH3:19])[C:11]([O:16][CH3:17])=[C:12]([O:29][CH3:26])[CH:13]=5)[S:6][CH:7]=4)[CH2:22][CH2:21]3)[N:4]=2)[CH:13]=[C:12]([O:14][CH3:15])[C:11]=1[O:16][CH3:17]

Participants

6

Reactant 4

HCID 4837PiperazineHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 12010380HCID 12010380, compound

Product 1

HCID 10232655N,N'-bis[[2-(3,4,5-Trimethoxyphenyl)thiazol-4-yl]methyl]piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloromethyl-2-(3,4,5-trimethoxyphenyl)thiazole (240 mg) and piperazine (34 mg) were dissolved in DMF (3 mL), potassium carbonate (166 mL) and potassium iodide (166 mg) were added to the solution, and the mixture was stirred at room temperature for 5 hours. After concentrating the reaction mixture under reduced pressure, chloroform was added to the residue, and the mixture was washed with water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform:methanol=40:1) to obtain the title compound as a free base.

Workup

  1. concentrationAfter concentrating the reaction mixture under reduced pressure, chloroform
  2. additionwas added to the residue
  3. washthe mixture was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=40:1)

Sources & evidence

ORD record
ord-e975b50b4bea4daa989b41c5dc76fad7
Source dataset
uspto-grants-2002_10
Patent number
US06472386B1

Reaction notes

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