Methyl iodide → 4-(Methoxymethyl)-1-(4-nitrophenyl)piperidine

HRID 2236834Notes

Reaction equation

HRID 2236834 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][OH:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].I[CH3:19].[H-].[Na+]>CN(C)C=O>[CH3:19][O:17][CH2:16][CH:13]1[CH2:12][CH2:11][N:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 23448266(1-(4-Nitrophenyl)piperidin-4-yl)methanol

Product 1

HCID 568053064-(Methoxymethyl)-1-(4-nitrophenyl)piperidineYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 0° C. mixture of [1-(4-nitro-phenyl)-piperidin-4-yl]-methanol and iodomethane (0.25 mL, 4.0 mmol) in N,N-dimethylformamide (3 mL) is added sodium hydride (60% dispersion in mineral oil, 80 mg, 2.0 mmol). The cooling bath is removed and the mixture is stirred at room temperature for five hours before it is re-cooled to 0° C. and quenched by the addition of saturated aqueous sodium hydrogen carbonate solution. The precipitated solid is collected by Büchner filtration, washed with water, and dried under house vacuum to give 4-methoxymethyl-1-(4-nitro-phenyl)-piperidine as pale yellow crystals (0.15 g, 60%).

Workup

  1. customThe cooling bath is removed
  2. temperatureis re-cooled to 0° C.
  3. customquenched by the addition of saturated aqueous sodium hydrogen carbonate solution
  4. filtrationThe precipitated solid is collected by Büchner filtration
  5. washwashed with water
  6. customdried under house vacuum

Sources & evidence

ORD record
ord-69221af87bc749f0bd52bffe29b655ad
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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