Hydrogen Peroxide → 2,3-Diaza-spiro[4.5]dec-2-ene

HRID 1024344

Reaction equation

HRID 1024344 reaction equation
[NH2:1][CH2:2][C:3]1([CH2:9][NH2:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.OO.[O-]Cl.[Na+]>O.CO>[CH2:2]1[C:3]2([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2)[CH2:9][N:10]=[N:1]1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 71994[1-(Aminomethyl)cyclohexyl]methanamineHCID 23665760Sodium Hypochlorite

Product 1

HCID 593394532,3-Diaza-spiro[4.5]dec-2-ene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

C-(1-Aminomethyl-cyclohexyl)-methylamine (10.0 g) was taken up in a mixture of H2O (40 mL) and MeOH (10 mL), and cooled in an ice bath. Simultaneously, H2O2 (44.3 mL of a 30% solution, 6 equiv.) and NaClO (125.5 mL of a 10% solution, 2.4 equiv.) were added dropwise, the ice bath was removed, and the mixture was stirred for 45 min. at room temperature. Extraction with DCM, drying over Na2SO4 and evaporation under reduced pressure, yielded 8.7 g of a clear, light-yellow liquid. 1H NMR (400 MHz, CDCl3) δ 1.24-1.53 (m, 10H), 4.17 (s, 4H).

Workup

  1. temperaturecooled in an ice bath
  2. customthe ice bath was removed
  3. extractionExtraction with DCM
  4. dry with materialdrying over Na2SO4 and evaporation under reduced pressure
  5. customyielded 8.7 g of a clear, light-yellow liquid

Sources & evidence

ORD record
ord-211e8b0ff83b457ca238a5a2e8938587
Source dataset
uspto-grants-2014_05
Patent number
US08722887B2

Linked notes

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