4-Hydroxypiperidine-1-carbonitrile → 1-(3-Isopropyl-1,2,4-oxadiazol-5-YL)piperidin-4-OL

HRID 68788

Reaktionsgleichung

Reaktionsgleichung von HRID 68788
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]#[N:9])[CH2:4][CH2:3]1.[OH:10][NH:11][C:12](=N)[CH:13]([CH3:15])[CH3:14]>C(OCC)(=O)C.CCOCC.[Cl-].[Cl-].[Zn+2]>[CH3:14][CH:13]([C:12]1[N:9]=[C:8]([N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)[O:10][N:11]=1)[CH3:15]

Komponenten

6

Edukt 2

HCID 218978254-Hydroxypiperidine-1-carbonitrileHCID 178449908HCID 178449908, Verbindung

Produkt 1

HCID 218977441-(3-Isopropyl-1,2,4-oxadiazol-5-YL)piperidin-4-OL

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007855ZincchlorideKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

4-Hydroxypiperidine-1-carbonitrile (3.0 g) and N-hydroxy-2-methylpropanimidamide (2.9 g) are dissolved in ethyl acetate (20 ml) and 1 M ZnCl2 in Et2O (29 ml) is added. A precipitate forms and the solvent is decanted off. Additional Et2O (20 ml) is added to wash the precipitate and again is decanted off. Ethanol (20 ml) is added followed by concentrated aqueous HCl (7.5 ml) and the mixture is heated to 100° C. for 3.5 h.

Aufarbeitung

  1. customA precipitate forms and the solvent is decanted off
  2. additionAdditional Et2O (20 ml) is added
  3. washto wash the precipitate
  4. customagain is decanted off
  5. additionEthanol (20 ml) is added

Quellen und Nachweise

ORD-Eintrag
ord-7965278f0abf44a5b7fbd8f75fc4af5e
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822471B2

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