Chlorotrimethylsilane → 4-(4-Trimethylsilyloxy-piperidin-1-yl)-3-fluoronitrobenzene

HRID 750905Notes

Reaction equation

HRID 750905 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=2[F:17])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:25][Si:26](Cl)([CH3:28])[CH3:27]>CN(C)C=O>[CH3:25][Si:26]([CH3:28])([CH3:27])[O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=2[F:17])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 37637811-(2-Fluoro-4-nitrophenyl)piperidin-4-one

Product 1

HCID 693102754-(4-Trimethylsilyloxy-piperidin-1-yl)-3-fluoronitrobenzeneYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

The mixture of 4-(4-oxo-piperidin-1-yl)-3-fluoronitrobenzene (0.250 mol), triethylamine (1.250 mol), trimethylsilylchloride (0.750 mol) in dimethylformamide was heated at 70° C. for 24 h. The solvent was removed under vacuum and to the residual mass was extracted with the ethyl acetate water mixture. The combined organic layer was dried and after removal of the solvent afforded title compound as a solid in 86% yield.

Workup

  1. customThe solvent was removed under vacuum and to the residual mass
  2. extractionwas extracted with the ethyl acetate water mixture
  3. customThe combined organic layer was dried
  4. customafter removal of the solvent

Sources & evidence

ORD record
ord-1257c62a67044f35b69da57fd762b085
Source dataset
uspto-grants-2008_07
Patent number
US07405228B2

Reaction notes

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