p-Fluoronitrobenzene → HCID 69352738, compound

HRID 1609806Notes

Reaction equation

HRID 1609806 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][CH2:13][C@H:12]([OH:16])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.F[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1>CN(C=O)C>[CH2:3]([N:10]1[CH2:15][CH2:14][CH2:13][C@H:12]([O:16][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 693762(S)-1-Benzyl-3-hydroxypiperidine

Product 1

HCID 69352738HCID 69352738, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of NaH (0.83 g, 37 mmol) in DMF (10 mL) was added 1-benzyl-(3S)-3-hydroxypiperidine (4.1 g, 21.5 mmol), and the resulting reaction mixture was stirred at ambient temperature for 2 hours. 4-Fluoronitrobenzene (2.5 mL, 23.6 mmol) in DMF (10 mL) was then added to the mixture dropwise. The resulting reaction mixture was stirred at ambient temperature for 2 hours. After removal of DMF in vacuo, the crude mixture was dissolved in ethyl acetate (200 mL), washed with water (100 mL×3), brine (100 mL), to give a yellow oil. Purification using silical gel chromatography column afforded 1-benzyl-(3S)-3-(4-nitrophenoxy)piperidine (6.5 g, 97% yield) as a yellow oil.

Workup

  1. customthe resulting reaction mixture
  2. customThe resulting reaction mixture
  3. stirringwas stirred at ambient temperature for 2 hours
  4. customAfter removal of DMF in vacuo
  5. dissolutionthe crude mixture was dissolved in ethyl acetate (200 mL)
  6. washwashed with water (100 mL×3), brine (100 mL)
  7. customto give a yellow oil
  8. customPurification

Sources & evidence

ORD record
ord-a65820bf415a4b40bf6a35330931f33e
Source dataset
uspto-grants-2006_01
Patent number
US06982259B2

Reaction notes

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