Piperidine → 5-Phenyl-3-(2-(1-piperidyl)ethoxy)isoxazole

HRID 612928Notes

Reaction equation

HRID 612928 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:7][N:6]=1.[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>CO>[C:10]1([C:8]2[O:7][N:6]=[C:5]([O:4][CH2:3][CH2:2][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH:9]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 195964873-(2-Bromoethoxy)-5-phenylisoxazole

Product 1

HCID 195965575-Phenyl-3-(2-(1-piperidyl)ethoxy)isoxazoleYield 92.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(2-Bromoethoxy)-5-phenylisoxazole (268 mg) was dissolved in methanol (1.0 ml), and piperidine (426 mg) was added thereto, followed by reflux of the resulting mixture for 3 hours. After the reaction mixture was added to ice-cold water (20 ml) and extracted with ether (20 ml×2), the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate) to obtain the title compound (251 mg, 92%) as colorless crystals.

Workup

  1. temperatureby reflux of the resulting mixture for 3 hours
  2. extractionextracted with ether (20 ml×2)
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-35a1b20fc1d74e029752a7d3c2b0ec6f
Source dataset
uspto-grants-1999_12
Patent number
US06005116

Reaction notes

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