Piperazine → Quipazine

HRID 1714759Notes

Reaction equation

HRID 1714759 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, saturated aqueous sodium hydrogencarbonate solution was added, and the system was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off 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. temperatureAfter cooling
  4. extractionthe system was extracted with chloroform
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified on silica gel column chromatography (chloroform:methanol=2:1)

Sources & evidence

ORD record
ord-34fba53cc6d2446baa16f6b0fbf31eca
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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