Phosphorus oxychloride → HCID 68352551, compound

HRID 541232Notes

Reaction equation

HRID 541232 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][C:6]([C:9]2(O)[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[C:1]([C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 68288666HCID 68288666, compound2×

Product 1

HCID 68352551HCID 68352551, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To solution of tert-butyl 4-(6-cyanopyridin-3-yl)-4-hydroxypiperidine-1-carboxylate (compound 51.2, 600 mg, 1.98 mmol, 1.00 equiv) in pyridine (15 mL) under nitrogen at 10-15° C. was carefully added POCl3 (3 g, 19.74 mmol, 9.97 equiv). After stirring overnight under nitrogen in a water/ice bath, the mixture was concentrated and the residue was dissolved in 50 mL of ethyl acetate. The organic phase was washed with 1×50 mL of hydrogen chloride (aq. 1M) followed by 1×50 mL of sodium bicarbonate (aq.sat.). The organic layer was then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified using silica gel column chromatography with ethyl acetate/petroleum ether (1:10) as the eluent to yield 0.26 g (46%) of the title compound as a white solid.

Workup

  1. customat 10-15° C.
  2. concentrationthe mixture was concentrated
  3. dissolutionthe residue was dissolved in 50 mL of ethyl acetate
  4. washThe organic phase was washed with 1×50 mL of hydrogen chloride (aq. 1M)
  5. dry with materialThe organic layer was then dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified

Sources & evidence

ORD record
ord-7bbbf4f17afb409eb17bfcfa04894de3
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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