Dichloromethane → 1-(3-(2-Fluoropyridin-3-yl)piperidin-1-yl)ethanone

HRID 1880146Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1880146
Cl.Cl.[F:3][C:4]1[C:9]([CH:10]2[CH2:15][CH2:14][CH2:13][NH:12][CH2:11]2)=[CH:8][CH:7]=[CH:6][N:5]=1.C(Cl)Cl.C(N(CC)CC)C.[C:26](OC(=O)C)(=[O:28])[CH3:27]>O>[F:3][C:4]1[C:9]([CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:26](=[O:28])[CH3:27])[CH2:11]2)=[CH:8][CH:7]=[CH:6][N:5]=1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 674169432-Fluoro-3-(piperidin-3-yl)pyridine dihydrochloride

Produkt 1

HCID 593268021-(3-(2-Fluoropyridin-3-yl)piperidin-1-yl)ethanoneAusbeute 18,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To an ice cooled solution of 2-fluoro-3-(piperidin-3-yl)pyridine dihydrochloride (612 mg, 2.418 mmol), DCM (20 mL) and triethylamine (2022 μL, 14.51 mmol) was added acetic anhydride (229 μL, 2.418 mmol) dropwise. After 1 hour, the reaction was poured into water and the aqueous mixture back extracted once with DCM (10 mL). The combined organics were washed with 0.5M NaOH and concentrated in vacuo. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (12 g), eluting with 0% to 100% EtOAc in hexane, to provide 1-(3-(2-fluoropyridin-3-yl)piperidin-1-yl)ethanone (100 mg, 0.450 mmol) as a light yellow syrup. [M+1]=223.1.

Aufarbeitung

  1. extractionthe aqueous mixture back extracted once with DCM (10 mL)
  2. washThe combined organics were washed with 0.5M NaOH
  3. concentrationconcentrated in vacuo
  4. customchromatographed through a Redi-Sep® pre-packed silica gel column (12 g)
  5. washeluting with 0% to 100% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-edf338f0215f465cabe36c791e200f76
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318718B2

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