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

HRID 12483

Reaction equation

HRID 12483 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-2504d08685a64c35a6ba654bf4472cd6
Source dataset
uspto-grants-2010_06
Patent number
US07728018B2

Linked notes

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