Acetonitrile → HCID 17906297, compound

HRID 852105Notes

Reaction equation

HRID 852105 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]3[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=3[O:13][N:12]=2)=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[2H][C:28]1([2H])[C:33]([2H])([2H])[C:32]([2H])([2H])[N:31]([2H])[C:30]([2H])([2H])[C:29]1([2H])[2H].C(#N)C>O>[F:20][C:18]1[CH:17]=[CH:16][C:15]2[C:11]([C:8]3[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][N:31]4[CH2:32][CH2:33][CH2:28][CH2:29][CH2:30]4)=[CH:6][CH:7]=3)=[N:12][O:13][C:14]=2[CH:19]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 16212919(~2~H_11_)PiperidineHCID 17906318HCID 17906318, compound

Product 1

HCID 17906297HCID 17906297, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine 3-[4-(2-bromo-ethoxy)-phenyl]-6-fluoro-benzo[d]isoxazole (550 mg, 1.63 mmol), potassium carbonate (500 mg, 3.62 mmol), piperidine- d11 (630 mg, 6.55 mmol) and 5% aqueous acetonitrile. Under a nitrogen atmosphere, heat to reflux overnight. Cool to room temperature and pour the reaction mixture into water resulting in white solid precipitation. Collect the solid and dry in vacuo. Dissolve the solid in ethyl acetate and filter to remove the insoluble materials and concentrate in vacuo. Take the solid up in diethyl ether, filter and precipitate the hydrochloride salt out of solution by addition of hydrogen chloride in diethyl ether. Collect the desired salt and dry in vacuo to give the title compound as a solid (410 mg, 67% Yield).

Workup

  1. temperatureUnder a nitrogen atmosphere, heat
  2. temperatureto reflux overnight
  3. customin white solid precipitation
  4. customCollect the solid
  5. customdry in vacuo
  6. dissolutionDissolve the solid in ethyl acetate
  7. filtrationfilter
  8. customto remove the insoluble materials
  9. concentrationconcentrate in vacuo
  10. filtrationfilter
  11. customprecipitate the hydrochloride salt out of solution
  12. additionby addition of hydrogen chloride in diethyl ether
  13. customCollect the desired salt
  14. customdry in vacuo

Sources & evidence

ORD record
ord-3a9d5c40a17549d5ab1af4fcb143ce18
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Reaction notes

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