Selectfluor → 3-Fluoro-1-(4-nitrophenyl)piperidin-4-one

HRID 750897Notes

Reaction equation

HRID 750897 reaction equation
C[Si](C)(C)[O:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.[B-](F)(F)(F)[F:22].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(#N)C>[F:22][CH:9]1[C:4](=[O:3])[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[CH2:8]1

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 69313311HCID 69313311, compound

Product 1

HCID 597541273-Fluoro-1-(4-nitrophenyl)piperidin-4-oneYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The mixture of 4-(4-trimethylsilyloxy-piperidin-1-yl)-nitrobenzene (101 mmol), selectfluor (101 mmol) in acetonitrile (100 ml) was stirred for 4 hours. The solvent was removed under reduced pressure and to the residual mass was extracted into ethyl acetate water mixture. The combined organic layer was dried and removal of the solvent afforded title compound in 95% yield.

Workup

  1. customThe solvent was removed under reduced pressure and to the residual mass
  2. extractionwas extracted into ethyl acetate water mixture
  3. customThe combined organic layer was dried
  4. customremoval of the solvent

Sources & evidence

ORD record
ord-bb8cf19bf8024b92a9fcda432858654c
Source dataset
uspto-grants-2008_07
Patent number
US07405228B2

Reaction notes

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