Hydrogen Peroxide → HCID 68642062, compound

HRID 1498961Notes

Reaction equation

HRID 1498961 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:5]=[CH:4][C:3]=1[N:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14]1.OO.C(=O)(O)[O-].[Na+]>C(O)=O.O>[CH2:15]1[N:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:17][CH2:18][N:13]2[C:3]3[CH:4]=[CH:5][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:7][C:2]=3[N:1]=[C:14]12

Participants

6

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 516892Sodium BicarbonateHCID 68642043HCID 68642043, compound

Product 1

HCID 68642062HCID 68642062, compoundYield 11.1%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Formic acid (0.29 g, 6.22 mmol) and purified water (5 ml) were added to ethyl 4-(2-amino-4-ethoxycarbonylphenyl)piperazine-1-carboxylate (2.0 g, 6.22 mmol) prepared in the Step 38-1-2. A 30% hydrogen peroxide solution (0.63 g, 18.67 mmol) was further added thereto, and the mixture was heated and stirred at 50° C. Formic acid (2 ml) and 2 ml of a 30% hydrogen peroxide solution were further added to the mixture. The resulting mixture was stirred for another one hour, then allowed to cool, and stirred. After being cooled to a room temperature, the mixture was neutralized with a saturated sodium bicarbonate solution and subjected to extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1 to 1:2) to give the title compound (0.22 g, 11%) as a white powder.

Workup

  1. customprepared in the Step 38-1-2
  2. temperaturethe mixture was heated
  3. stirringThe resulting mixture was stirred for another one hour
  4. temperatureto cool
  5. stirringstirred
  6. temperatureAfter being cooled to a room temperature
  7. extractionsubjected to extraction with ethyl acetate
  8. dry with materialThe extract was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. customThe concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1 to 1:2)

Sources & evidence

ORD record
ord-bc7ab956b681411a86d296cb7fe93f5b
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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