Hydrogen Peroxide → 2,3-Diaza-spiro[4.4]non-2-ene

HRID 1024341

Reaction equation

HRID 1024341 reaction equation
[NH2:1][CH2:2][C:3]1([CH2:8][NH2:9])[CH2:7][CH2:6][CH2:5][CH2:4]1.OO.[O-]Cl.[Na+]>O.CO>[CH2:2]1[C:3]2([CH2:7][CH2:6][CH2:5][CH2:4]2)[CH2:8][N:9]=[N:1]1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 4325931,1-CyclopentanedimethanamineHCID 23665760Sodium Hypochlorite

Product 1

HCID 547519672,3-Diaza-spiro[4.4]non-2-eneYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

C-(1-Aminomethyl-cyclopentyl)-methylamine (4.87 g) was taken up in a mixture of H2O (40 mL) and MeOH (10 mL), and cooled in an ice bath. Simultaneously, H2O2 (23.9 mL of a 30% solution, 6 equiv.) and NaClO (54.3 mL of a 10% solution, 2.4 equiv.) were added dropwise, the ice bath was removed, and the mixture was stirred for 2 h. at room temperature. Extraction with DCM, drying over Na2SO4 and evaporation under reduced pressure yielded 3.74 g of a clear, light-yellow liquid containing 90% of the anticipated product and 10% of the diamine starting material. This material was used in subsequent steps without further purification. 1H NMR (400 MHz, CDCl3) δ 1.48-1.57 (m, 4H), 1.62-1.69 (m, 4H), 4.26 (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 3.74 g of a clear, light-yellow liquid

Sources & evidence

ORD record
ord-55d2e026631849a787b83cefb1f58a45
Source dataset
uspto-grants-2014_05
Patent number
US08722887B2

Linked notes

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