p-Fluoronitrobenzene → HCID 25139344, compound

HRID 1523395Notes

Reaction equation

HRID 1523395 reaction equation
[H-].[Na+].[CH:3]1([N:7]2[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4]1.F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1>CN(C)C=O>[CH:3]1([N:7]2[CH2:8][CH2:9][CH:10]([O:13][C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)[CH2:11][CH2:12]2)[CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 581554161-Cyclobutylpiperidin-4-ol

Product 1

HCID 25139344HCID 25139344, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a stirred solution of sodium hydride (24.76 g, 60% in mineral oil, 0.619 moles) in dimethylformamide (100 mL) was added 1-cyclobutyl-4-piperidinol (80 g, 0.516 moles, obtained in the above step) in dimethylformamide (300 mL) at 10° C. under a nitrogen atmosphere. The mass was stirred for 1 hour. A solution of 4-fluoronitrobenzene (87.3 g, 0.619 moles) in dimethylformamide (300 mL) was added drop wise to the above reaction mass at room temperature. After completion of reaction, the mass was quenched on to chilled water (2 L) and stirred for 1 hour. The obtained solids were separated and dissolved in ethyl acetate (1 L). The resulting ethyl acetate layer was washed with water, dried over sodium sulfate and concentrated under vacuum. The residue, thus obtained, was purified by flash chromatography (methanol:chloroform, 2:8) to afford the title compound 99.7 g (Yield: 70%).

Workup

  1. customAfter completion of reaction
  2. customthe mass was quenched on
  3. temperatureto chilled water (2 L)
  4. stirringstirred for 1 hour
  5. customThe obtained solids were separated
  6. dissolutiondissolved in ethyl acetate (1 L)
  7. washThe resulting ethyl acetate layer was washed with water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under vacuum
  10. customThe residue, thus obtained
  11. customwas purified by flash chromatography (methanol:chloroform, 2:8)

Sources & evidence

ORD record
ord-3700efed81094d31931cfd9500c031db
Source dataset
uspto-grants-2015_07
Patent number
US09079888B2

Reaction notes

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