Water → HCID 86648988, compound

HRID 518051Notes

Reaction equation

HRID 518051 reaction equation
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[CH:12]=[N:11][CH:10]=[C:9]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]2[CH3:19])[N:8]=1.O.CN([CH:24]=[O:25])C>>[Cl:6][C:7]1[C:12]([CH:24]=[O:25])=[N:11][CH:10]=[C:9]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]2[CH3:19])[N:8]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 534091142-Chloro-6-(2-methyl-1-piperidinyl)pyrazine

Product 1

HCID 86648988HCID 86648988, compoundYield 57%

Procedure

Phosphoryl chloride (1.62 mL) was added dropwise to DMF (5 ml) at 0° C. The mixture was stirred for 15 min, and a solution of 2-chloro-6-(2-methylpiperidin-1-yl)pyrazine (1.85 g) in DMF (1 mL) was added dropwise thereto. The mixture was stirred at 80° C. for 16 hr, water (5 mL) was added at 0° C., and the mixture was stirred at room temperature for 1.5 hr. The mixture was extracted with ethyl acetate. The aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with water and saturated brine, dried over magnesium sulfate, and concentrated. The residue was purified by recrystallization (ethyl acetate-hexane) to give the title compound (1.18 g, 57%) as a colorless powder.

Workup

  1. stirringThe mixture was stirred at 80° C. for 16 hr
  2. stirringthe mixture was stirred at room temperature for 1.5 hr
  3. extractionThe mixture was extracted with ethyl acetate
  4. extractionThe aqueous layer was extracted again with ethyl acetate
  5. washThe combined organic layer was washed with water and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by recrystallization (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-9b0652e66c5846a5a8610179b5cd6c9f
Source dataset
uspto-grants-2015_08
Patent number
US09115139B2

Reaction notes

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