HCID 68476842, compound → HCID 59439200, compound

HRID 1515122Notes

Reaction equation

HRID 1515122 reaction equation
[Cl:1][C:2]([Cl:19])([Cl:18])[CH2:3][O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]([O:15]CC)=[O:14])[CH2:9][CH2:8]1)=[O:6]>[OH-].[K+].C(O)C.O>[Cl:19][C:2]([Cl:1])([Cl:18])[CH2:3][O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]([OH:15])=[O:14])[CH2:9][CH2:8]1)=[O:6]

Participants

4

Reactant 1

HCID 68476842HCID 68476842, compound

Product 1

HCID 59439200HCID 59439200, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 21946426Potassium hydroxide ethanolSolvent

Procedure

Ethyl 1-(2,2,2-trichloroethoxycarbonyl)piperidine-4-carboxylate (158 g, 0.48 mol) was dissolved in a 2 N potassium hydroxide-ethanol solution (500 mL) and water (500 mL), followed by heating under reflux for about 1 hour. After cooling, to the reaction mixture was added water (300 mL), followed by extraction with ethyl acetate (300 mL×3). The aqueous layer was added a 10% aqueous citric acid solution, followed by extraction with ethyl acetate (500 mL×3), and the acidic fraction extracted was washed with saturated brine (300 mL). The resultant was dried over anhydrous sodium sulfate and then filtered, and the solvent was evaporated. The residue was washed with hexane to obtain 62.9 g of 1-(2,2,2-trichloroethoxycarbonyl)piperidine-4-carboxylic acid as a colorless crystal (yield 43%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for about 1 hour
  3. temperatureAfter cooling, to the reaction mixture
  4. extractionfollowed by extraction with ethyl acetate (300 mL×3)
  5. additionThe aqueous layer was added a 10% aqueous citric acid solution
  6. extractionfollowed by extraction with ethyl acetate (500 mL×3)
  7. extractionthe acidic fraction extracted
  8. washwas washed with saturated brine (300 mL)
  9. dry with materialThe resultant was dried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customthe solvent was evaporated
  12. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-7fdfa8451e964900abb4285ea2763d34
Source dataset
uspto-grants-2012_07
Patent number
US08222407B2

Reaction notes

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