Water → HCID 86681229, compound

HRID 1848256Notes

Reaction equation

HRID 1848256 reaction equation
Cl[C:2]1[C:3]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.[OH-:14].[Na+].O>CS(C)=O>[O:11]1[CH2:12][CH2:13][N:8]([C:3]2[C:2](=[O:14])[NH:7][CH:6]=[CH:5][N:4]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 205289944-(3-Chloropyrazin-2-YL)morpholine

Product 1

HCID 86681229HCID 86681229, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(3-chloropyrazin-2-yl)morpholine (894 mg, 6 mmol) and aq NaOH (13 mL, 52 mmol) in DMSO (18 mL) was stirred at 80° C. for 2 h. The reaction mixture was poured into water (30 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give 3-morpholinopyrazin-2(1H)-one as a light yellow solid (807 mg, 92.9%). 1H NMR (300 MHz, CDCl3) δ 11.80 (br s, 1H), 7.05 (d, J=4.2 Hz, 1H), 6.73 (d, J=4.2 Hz, 1H), 3.84 (s, 8H). LCMS (ESI) m/z 182 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-20f3fa5ed99a4bf289fd2bfc2bd56382
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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