Phosphorus oxychloride → 1-(3-Chloropyridin-2-yl)-1,2,3,6-tetrahydropyridine-4-carbonitrile

HRID 404567Notes

Reaction equation

HRID 404567 reaction equation
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[C:8]([N:13]2[CH2:18][CH2:17][C:16](O)([C:19]#[N:20])[CH2:15][CH2:14]2)=[N:9][CH:10]=[CH:11][CH:12]=1>N1C=CC=CC=1>[Cl:6][C:7]1[C:8]([N:13]2[CH2:14][CH:15]=[C:16]([C:19]#[N:20])[CH2:17][CH2:18]2)=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 714170321-(3-Chloropyridin-2-yl)-4-hydroxypiperidine-4-carbonitrile2×

Product 1

HCID 583194961-(3-Chloropyridin-2-yl)-1,2,3,6-tetrahydropyridine-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

At 0° C., phosphoryl trichloride (10 g, 68 mmol) was slowly added into a solution of 1-(3-chloropyridin-2-yl)-4-hydroxypiperidine-4-carbonitrile (compound 22) (8 g, 33 mmol) in pyridine. After stirred at RT for 30 minutes, the reaction was washed by a HCl solution, and extracted by ethyl acetate. The organic layer was evaporated to give a crude product, which was purified using column chromatography to give the product.

Workup

  1. washthe reaction was washed by a HCl solution
  2. extractionextracted by ethyl acetate
  3. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-0baa843af5a34f44b8d1d413461c08d2
Source dataset
uspto-grants-2014_06
Patent number
US08748610B2

Reaction notes

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