Dimethylformamide → 1-(2-Nitrophenyl)piperidine

HRID 2099103Notes

Reaction equation

HRID 2099103 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C)C=O.F[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20]>O>[N+:19]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8082PiperidineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 2254571-(2-Nitrophenyl)piperidineYield 98.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Piperidine (338 μl, 3.41 mmol, commercially available product) was added at room temperature to an N,N-dimethylformamide (DMF; 0.5 ml) solution of 2-fluoro-1-nitrobenzene (219 mg, 1.55 mmol, commercially available product). The resulting mixture was stirred for two hours. Water was added to the mixture, and the resulting mixture was extracted three times with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20 g, hexane/ethyl acetate=20/1). Thus, 1-(2-nitrophenyl)piperidine (315 mg, 98.8%) was yielded as a colorless oily material.

Workup

  1. extractionthe resulting mixture was extracted three times with ethyl acetate
  2. washThe obtained organic layer was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (20 g, hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-e5c5d98e9dd9490b8b3441eee1207609
Source dataset
uspto-grants-2009_08
Patent number
US07569536B2

Reaction notes

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