Selectfluor → 3-Fluoro-1-(2-fluoro-4-nitrophenyl)piperidin-4-one

HRID 750906Notes

Reaction equation

HRID 750906 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][C:11]=2[F:19])[CH2:6][CH2:5]1.[B-](F)(F)(F)[F:23].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(#N)C>[F:23][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][C:11]=2[F:19])[CH2:8]1

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 693102754-(4-Trimethylsilyloxy-piperidin-1-yl)-3-fluoronitrobenzene

Product 1

HCID 597540583-Fluoro-1-(2-fluoro-4-nitrophenyl)piperidin-4-oneYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The mixture of 4-(4-trimethylsilyloxy-piperidin-1-yl)-3-fluoronitrobenzene (151 mmol), selectfluor (151 mmol) in acetonitrile 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 88% 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-236c3e1f308b4604a5d01d54f1f68fa7
Source dataset
uspto-grants-2008_07
Patent number
US07405228B2

Reaction notes

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