Trifluoroacetic acid → 2-(Piperidin-4-yl)quinoxaline

HRID 1066077Notes

Reaction equation

HRID 1066077 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:23]=[N:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl.[OH-].[Na+]>[N:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:22]=[CH:23][C:14]=1[CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 211980351-Tert-butoxycarbonyl-4-(quinoxalin-2-yl)piperidine

Product 1

HCID 211980262-(Piperidin-4-yl)quinoxalineYield 42%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 0.47 gm (1.5 mMol) 1-tert-butoxycarbonyl-4-(quinoxalin-2-yl)piperidine and 5 mL trifluoroacetic acid in 5 mL dichloromethane was stirred at room temperature for 18 hours. The reaction mixture was diluted with 2N sodium hydroxide and the phases were separated. The aqueous phase was extracted well with dichloromethane. The organic phases were combined, washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, eluting with dichloromethane containing from 10% to 40% methanol and a trace of ammonium hydroxide. Fractions containing product were combined and concentrated under reduced pressure to provide 0.133 gm (42%) of the title compound as a tan foam.

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted well with dichloromethane
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluting with dichloromethane containing from 10% to 40% methanol
  7. additionFractions containing product
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-01204f7df4824d869145027ed5968dee
Source dataset
uspto-grants-2001_06
Patent number
US06242450B1

Reaction notes

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