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

HRID 2236834Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2236834
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-69221af87bc749f0bd52bffe29b655ad
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07713994B2

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