Piperazine → Quipazine

HRID 1714780Notes

Reaction equation

HRID 1714780 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.C(=O)([O-])O.[Na+]>C(O)CO>[N:1]1([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 119282-ChloroquinolineHCID 516892Sodium Bicarbonate

Product 1

HCID 5011QuipazineYield 102.2%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
140 °C

Procedure

To a solution formed by dissolving 4.31 g of anhydrous piperazine in 30 ml of ethylene glycol, 818 mg of 2-chloroquinoline was added, and stirred at 140° C. for 2 hours. After cooling the reaction mixture, saturated aqueous sodium hydrogencarbonate solution was added, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified on silica gel column chromatography (chloroform:methanol=2:1) to provide 1.09 g (100%) of 2-piperazin-1-ylquinoline.

Workup

  1. customTo a solution formed
  2. additionwas added
  3. additionwas added
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified on silica gel column chromatography (chloroform:methanol=2:1)

Sources & evidence

ORD record
ord-4fa9ca7447264c219f8376d75b571aba
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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