849833-56-3 → 1-(3-Isopropyl-1,2,4-oxadiazol-5-YL)piperidin-4-OL

HRID 1467993Notes

Reaction equation

HRID 1467993 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]#[N:9])[CH2:4][CH2:3]1.[OH:10]/[N:11]=[C:12](/N)\[CH:13]([CH3:15])[CH3:14]>C1COCC1.[Cl-].[Cl-].[Zn+2]>[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])[CH3:14]

Participants

5

Reactant 2

HCID 5712089849833-56-3HCID 218978254-Hydroxypiperidine-1-carbonitrile

Product 1

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

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-hydroxypiperidine-1-carbonitrile (0.4 g, 3.1 mmol) in THF (10 mL), (E)-N′-hydroxyisobutyrimidamide (0.35 g, 35 mmol) and ZnCl2 (1M solution in THF) (4.7 mL) were added and stirred at room temperature for 10 h. The reaction mixture was concentrated in vacuo and the resulting crude was dissolved in 4N HCl in ethanol-water (1:1) and stirred at 60-70° C. for 2-3 h. The reaction was quenched by saturated NaHCO3 and the organic layer was separated and concentrated. The residue on column chromatography gave the title compound. (0.280 g, 41.8%)

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe resulting crude was dissolved in 4N HCl in ethanol-water (1:1)
  3. stirringstirred at 60-70° C. for 2-3 h
  4. customThe reaction was quenched by saturated NaHCO3
  5. customthe organic layer was separated
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-89143c5012fb4e74b989f2a9b77c262d
Source dataset
uspto-grants-2015_04
Patent number
US09000175B2

Reaction notes

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