Citric Acid → 8-(1-Piperazinylsulfonyl)quinoline

HRID 1829123Notes

Reaction equation

HRID 1829123 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=O)(C)(C)C.C(N(CC)CC)C.[N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][C:29]=2[S:31](Cl)(=[O:33])=[O:32])[CH:24]=[CH:23][CH:22]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl>[N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][C:29]=2[S:31]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)(=[O:33])=[O:32])[CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8471TriethylamineHCID 292208-Quinolinesulfonyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 220289298-(1-Piperazinylsulfonyl)quinolineYield 22.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-tert-Butoxycarbonylpiperazine (2.22 g) and triethylamine (2.0 mL) were dissolved in dichloromethane (100 mL), and 8-quinolinesulfonyl chloride (2.71 g) was added thereto. The mixture was stirred at room temperature for 14 hr. 10% citric acid solution was added to the reaction mixture and the mixture was extracted with chloroform. The extract was washed with brine, dried and concentrated under reduced pressure. The residue was dissolved in dichloromethane (20 mL), and trifluoroacetic acid (5 mL) was added thereto. The mixture was stirred at room temperature for 1.5 hr. The reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium hydrogencarbonate solution was added to the residue. The mixture was extracted with chloroform, and the extract was dried and concentrated under reduced pressure to give 1-(8-quinolinesulfonyl)piperazine (0.73 g) as a white solid.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe extract was washed with brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in dichloromethane (20 mL)
  6. additiontrifluoroacetic acid (5 mL) was added
  7. stirringThe mixture was stirred at room temperature for 1.5 hr
  8. concentrationThe reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium hydrogencarbonate solution
  9. additionwas added to the residue
  10. extractionThe mixture was extracted with chloroform
  11. customthe extract was dried
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-69aa6dd8ce2d43f3a3fc1f757bb5b77d
Source dataset
uspto-grants-2006_06
Patent number
US07060722B2

Reaction notes

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