Potassium Carbonate → HCID 66642970, compound

HRID 869249Notes

Reaction equation

HRID 869249 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:9]2[CH:10]=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:8]=2[O:7][CH2:6][C:5]1=[O:17].C(=O)([O-])[O-].[K+].[K+].[CH3:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C(=O)([O-])O.[Na+]>C(#N)C>[CH3:24][N:25]1[CH2:30][CH2:29][N:28]([CH2:2][CH2:3][N:4]2[C:9]3[CH:10]=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:8]=3[O:7][CH2:6][C:5]2=[O:17])[CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 66642902HCID 66642902, compound

Product 1

HCID 66642970HCID 66642970, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 4-(2-chloroethyl)-7-nitro-2H-1,4-benzoxazine-3(4H)-one (Preparation Example 430) (1.08 g), potassium carbonate (0.87 g) and acetonitrile (10.8 mL), 1-methylpiperazine (1.39 mL) was added and stirred at 80° C. for 48 hours. After the reaction liquid was cooled, saturated aqueous sodium hydrogen carbonate was added, and the reaction liquid was extracted with ethyl acetate and the extract was washed with saturated aqueous sodium chloride. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; chloroform:methanol=100:0 to 20:1) to give 4-[2-(4-methylpiperazin-1-yl)ethyl]-7-nitro-2H-1,4-benzoxazine-3(4H)-one (690 mg) as a yellow liquid.

Workup

  1. additionwas added
  2. customAfter the reaction liquid
  3. temperaturewas cooled
  4. customthe reaction liquid
  5. extractionwas extracted with ethyl acetate
  6. washthe extract was washed with saturated aqueous sodium chloride
  7. dry with materialAfter drying over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluent; chloroform:methanol=100:0 to 20:1)

Sources & evidence

ORD record
ord-2a2769067fcd478bb3a3fc039d009e4f
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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