1-Benzylpiperidin-4-ol → 2-[(1-Benzylpiperidin-4-yl)oxy]-3-methylpyridine

HRID 222325

Reaktionsgleichung

Reaktionsgleichung von HRID 222325
CC(C)([O-])C.[K+].[CH2:7]([N:14]1[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.F[C:22]1[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][N:23]=1>CS(C)=O>[CH2:7]([N:14]1[CH2:19][CH2:18][CH:17]([O:20][C:22]2[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][N:23]=2)[CH2:16][CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

5

Edukt 3

HCID 784611-Benzylpiperidin-4-olHCID 2427222-Fluoro-3-methylpyridineHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 577538832-[(1-Benzylpiperidin-4-yl)oxy]-3-methylpyridineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Potassium tert-butoxide (1.08 g, 8.62 mmol) was added to a solution of 1-benzyl-4-hydroxypiperidine (1.5 g, 7.84 mmol) in dimethylsulfoxide (5 mL) and the mixture was stirred at room temperature for 1 hour. 2-Fluoro-3-methylpyridine (957 mg, 8.62 mmol) was then added and the reaction mixture was stirred at room temperature for 3 hours. The mixture was partitioned between ethyl acetate and water, and the organic layer was separated and washed with sodium hydrogen carbonate solution and brine. The organic solution was then dried over magnesium sulfate concentrated in vacuo and the residue was purified by column chromatography on silica gel, eluting with dichloromethane:methanol, 100:0 to 70:30, to afford the title compound as a solid in 85% yield, 1.9 g. 1H NMR (CDCl3, 400 MHz) □: 1.79-1.94 (m, 2H), 1.98-2.09 (m, 2H), 2.17 (s, 3H), 2.37-2.47 (m, 2H), 2.68-2.77 (m, 2H), 3.61-3.51 (bs, 2H), 5.12-5.20 (m, 1H), 6.74 (m, 1H), 7.24-7.37 (m, 6H), 7.95 (m, 1H); LRMS APCI m/z 283 [M+H]+

Aufarbeitung

  1. stirringthe reaction mixture was stirred at room temperature for 3 hours
  2. customThe mixture was partitioned between ethyl acetate and water
  3. customthe organic layer was separated
  4. washwashed with sodium hydrogen carbonate solution and brine
  5. dry with materialThe organic solution was then dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customthe residue was purified by column chromatography on silica gel
  8. washeluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-60dfe48d9b6b47ba8ff6d5333a153cea
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207198B2

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