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Piperazine → 7-(Piperazin-1-yl)furo[2,3-c]pyridine

HRID 1714798
Notes
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Reaction equation

HRID 1714798 reaction equation
Cl[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][O:8][C:7]=12.C(=O)([O-])O.[Na+].[NH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>C(O)CO>[N:16]1([C:2]2[N:3]=[CH:4][CH:5]=[C:6]3[CH:10]=[CH:9][O:8][C:7]=23)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 4837PiperazineHCID 516892Sodium BicarbonateHCID 128261077-Chlorofuro[2,3-c]pyridine

Product 1

HCID 183997267-(Piperazin-1-yl)furo[2,3-c]pyridineYield 75%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
140 °C

Procedure

In 100 ml of ethylene glycol 8.6 g of anhydrous piperazine was dissolved, and to which 7-chlorofuro[2,3-c]pyridine was added, followed by an overnight's stirring at 140° C. After cooling, saturated aqueous sodium hydrogencarbonate solution was added to the solution, which was then 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 to provide 1.52 g (75%) of 7-piperazin-1-ylfuro[2,3-c]pyridine.

Workup

  1. temperatureAfter cooling
  2. extractionwas then extracted with chloroform
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified on silica gel column chromatography

Sources & evidence

ORD record
ord-205f417251854367a6bd6884850545e7
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07799775B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes