Trifluoroacetic acid → 4-(3-Phenyl-5-isoxazolyl)piperidine

HRID 1985476Notes

Reaction equation

HRID 1985476 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([CH:12]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>ClCCl>[C:1]1([C:7]2[CH:11]=[C:10]([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59731907tert-Butyl 4-(3-phenylisoxazol-5-yl)piperidine-1-carboxylate

Product 1

HCID 597320154-(3-Phenyl-5-isoxazolyl)piperidineYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl 4-(3-phenylisoxazol-5-yl)piperidine-1-carboxylate (225 mg, 0.78 mmol) was diluted in dichloromethane (3 mL). Trifluoroacetic acid (3 mL) was added to the mixture. Reaction stirred at room temperature for 1 hour. Mixture was diluted with dichloromethane and then concentrated in vacuo. Residue was treated with aqueous sodium bicarbonate. Mixture was extracted 2× ethyl acetate. Combined extracts were washed 1× water, 1× brine. Organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. Title compound was obtained as white solid in 76% yield. MS m/e (M+H)+=229.1.

Workup

  1. customReaction
  2. concentrationconcentrated in vacuo
  3. additionResidue was treated with aqueous sodium bicarbonate
  4. extractionMixture was extracted 2× ethyl acetate
  5. washCombined extracts were washed 1× water, 1× brine
  6. dry with materialOrganic layer was dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e1716bda18e4911a2c0a02b709fe3a4
Source dataset
uspto-grants-2009_06
Patent number
US07544680B2

Reaction notes

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