2-Bromopyridine → Ethyl 2-(1-(pyridin-2-yl)piperidin-4-yl)acetate

HRID 534190Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 534190
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].Br[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1>CN(C=O)C.O>[N:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][CH2:3]1

Komponenten

6

Edukt 3

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 45358839Piperidin-4-yl-acetic acid ethyl ester hydrochloride

Produkt 1

HCID 68385347Ethyl 2-(1-(pyridin-2-yl)piperidin-4-yl)acetateAusbeute 25,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To a stirred solution of ethyl 2-(piperidin-4-yl)acetate, hydrochloride (2.0 g, 9.63 mmol) in DMF (40 mL) was added K2CO3 (3.99 g, 28.9 mmol) followed by 2-bromopyridine (1.521 g, 9.63 mmol) and stirred at 130° C. for 16 h. Reaction mixture was diluted with water (200 mL) and extracted with ethyl acetate (2×100 mL). The combined organic layer was washed with water (2×100 mL), brine (100 mL) and dried over Na2SO4 filtered and concentrated under reduced pressure. The residues was purified by column chromatography using 100-200 silica gel by eluting with 20% ethyl acetate in petroleum ether to afford ethyl 2-(1-(pyridin-2-yl)piperidin-4-yl)acetate (600 mg, 19.86% yield) as color less liquid. LCMS (ES) m/e 249.20 (M+H)+.

Aufarbeitung

  1. customReaction mixture
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washThe combined organic layer was washed with water (2×100 mL), brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residues was purified by column chromatography
  8. washby eluting with 20% ethyl acetate in petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-5afc7cc2a0f8427694dda938d6077503
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853408B2

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