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

HRID 68788

Reaction equation

HRID 68788 reaction equation
[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]

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7965278f0abf44a5b7fbd8f75fc4af5e
Source dataset
uspto-grants-2014_09
Patent number
US08822471B2

Linked notes

Loading…