Tetrapropylammonium → 1-(3-Isopropyl-1,2,4-oxadiazol-5-YL)piperidin-4-one

HRID 1409739

Reaktionsgleichung

Reaktionsgleichung von HRID 1409739
[CH3:1][CH:2]([C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]2)[O:6][N:5]=1)[CH3:3].C[N+]1([O-])CCOCC1.C([N+](CCC)(CCC)CCC)CC>ClCCl>[CH3:3][CH:2]([C:4]1[N:8]=[C:7]([N:9]2[CH2:10][CH2:11][C:12](=[O:15])[CH2:13][CH2:14]2)[O:6][N:5]=1)[CH3:1]

Komponenten

5

Edukt 3

HCID 9559TetrapropylammoniumHCID 82029Methyl morpholine oxideHCID 218977441-(3-Isopropyl-1,2,4-oxadiazol-5-YL)piperidin-4-OL

Produkt 1

HCID 669153481-(3-Isopropyl-1,2,4-oxadiazol-5-YL)piperidin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-[3-(Propan-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-4-ol (0.5 g) is dissolved in dichloromethane (75 mL) and 4 A molecular sieves (4 g) are added followed by N-methylmorpholine-N-oxide (1.52 g) and tetrapropylammonium perrhutenate (0.018 g) and the mixture is stirred at room temperature for 1 h. The reaction is then filtered through celite and the mother liquor washed with water (2×50 mL). The water layers are then combined and back extracted with dichloroemthane (100 mL). The dichloromethane layers are combined, dried over Na2SO4, filtered and concentrated to give the title compound. LC (method 20): tR=1.67 min; Mass spectrum (APCI): m/z=210 [M+H]+.

Aufarbeitung

  1. addition4 A molecular sieves (4 g) are added
  2. filtrationThe reaction is then filtered through celite
  3. washthe mother liquor washed with water (2×50 mL)
  4. extractionback extracted with dichloroemthane (100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-38fbc51127124e7badac6fcceb6e2ec6
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921398B2

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