Picolinoyl Chloride Hydrochloride → HCID 59577127, Verbindung

HRID 2041988Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2041988
Cl.[C:2]([C:6]1[CH:17]=[CH:16][CH:15]=[CH:14][C:7]=1[O:8][CH:9]1[CH2:13][CH2:12][NH:11][CH2:10]1)([CH3:5])([CH3:4])[CH3:3].Cl.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25](Cl)=[O:26]>N1C=CC=CC=1>[C:2]([C:6]1[CH:17]=[CH:16][CH:15]=[CH:14][C:7]=1[O:8][CH:9]1[CH2:13][CH2:12][N:11]([C:25]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][N:19]=2)=[O:26])[CH2:10]1)([CH3:5])([CH3:3])[CH3:4]

Komponenten

4

Edukt 2

HCID 135033Picolinoyl Chloride HydrochlorideHCID 53409533HCID 53409533, Verbindung

Produkt 1

HCID 59577127HCID 59577127, VerbindungAusbeute 43,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-(2-tert-butylphenoxy)pyrrolidine hydrochloride (0.26 g, 1.00 mmol) in pyridine (2.5 mL) was added picolinoyl chloride hydrochloride (0.20 g, 1.10 mmol) at room temperature. After 16 h the reaction mixture was concentrated under reduced pressure, the residue partitioned between ethyl acetate (50.0 mL) and water (50.0 mL) and separated. The organic layer was washed with saturated sodium chloride (50.0 mL), dried (MgSO4), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 80:20 to 50:50 heptane/ethyl acetate) provided (3-(2-tert-butylphenoxy)pyrrolidin-1-yl)(pyridin-2-yl)methanone (0.14 g, 43%) as a pale yellow oil.

Aufarbeitung

  1. concentrationAfter 16 h the reaction mixture was concentrated under reduced pressure
  2. customthe residue partitioned between ethyl acetate (50.0 mL) and water (50.0 mL)
  3. customseparated
  4. washThe organic layer was washed with saturated sodium chloride (50.0 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash column chromatography (silica gel, 80:20 to 50:50 heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-83eb8185ef65483aadad863ff41c6b2b
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586571B2

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