Methanol → 1-(2-Methoxy-4-nitrophenyl)piperidine

HRID 2241899Notes

Reaction equation

HRID 2241899 reaction equation
[CH3:1][OH:2].[H-].[Na+].F[C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>CN(C)C=O>[CH3:1][O:2][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 107043451-(2-Fluoro-4-nitrophenyl)piperidine

Product 1

HCID 28254311-(2-Methoxy-4-nitrophenyl)piperidineYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of methanol (0.178 ml, 10.0 mmol) in N,N-dimethylformamide (1 ml) was added dropwise to a suspension of 60% sodium hydride (0.176 g, 4.40 mmol) in N,N-dimethylformamide (5 ml) under ice cooling, and the mixture was stirred at room temperature for 1 hour. 1-(2-Fluoro-4-nitrophenyl)piperidine (compound of Reference Example 3; 0.448 g, 2.00 mmol) was added to the reaction mixture under ice cooling, and the mixture was refluxed for 20 hours. Ice water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1) to give the title compound (0.395 g, 84%) as a yellow solid.

Workup

  1. temperaturethe mixture was refluxed for 20 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe residue obtained by evaporation of the solvent under reduced pressure
  6. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-bdbf2aea8f8f4113b339b93b891b266a
Source dataset
uspto-grants-2010_03
Patent number
US07671058B2

Reaction notes

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