Hydrogen Peroxide → HCID 20294523, compound

HRID 1389997Notes

Reaction equation

HRID 1389997 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)#[N:2].[OH:19]O.[OH-].[Na+].CO>O>[NH2:2][C:1](=[O:19])[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 14798Sodium HydroxideHCID 20294529HCID 20294529, compound

Product 1

HCID 20294523HCID 20294523, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 5.0 g (0.02 mole) of 1-(3-cyanopropyl)-4-(1,1-dimethylethoxycarbonyl)piperazine, 10 ml of 30% hydrogen peroxide solution and 10 ml of 20% NaOH solution warmed spontaneously to 42°. After the initial exothermic reaction had subsided and the temperature returned to room temperature, 50 ml of methanol was added dropwise; a temperature rise to 38° was noted. After heating two hours at 50° the mixture was diluted with 50 ml of water and extracted with CH2Cl2. The organic extracts were dried (Mg SO4), filtered and evaporated on a rotary evaporator. The crude product was recrystallized from ethyl acetatehexane to yield 0.4 g (7%) of 1-(4-amino-4-oxobutyl)-4-(1,1-dimethylethoxycarbonyl)piperazine, 1/4 hydrate, mp-67.5°-71.5°. Calc. for C13H15N3O3. 1/4 H2O (275.87): C, 56.60; H, 9.32; N, 15.23. Found: C, 56.58; H, 9.41; N, 15.23.

Workup

  1. temperaturewarmed spontaneously to 42°
  2. customAfter the initial exothermic reaction
  3. customreturned to room temperature
  4. customto 38°
  5. temperatureAfter heating two hours at 50° the mixture
  6. extractionextracted with CH2Cl2
  7. dry with materialThe organic extracts were dried (Mg SO4)
  8. filtrationfiltered
  9. customevaporated on a rotary evaporator
  10. customThe crude product was recrystallized from ethyl acetatehexane

Sources & evidence

ORD record
ord-50e59564d0c943fab86d6c023e5f8580
Source dataset
uspto-grants-1981_01
Patent number
US04247549

Reaction notes

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