Hydrogen Peroxide → 2,3-Diaza-spiro[4.5]dec-2-ene
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]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
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
- temperaturecooled in an ice bath
- customthe ice bath was removed
- extractionExtraction with DCM
- dry with materialdrying over Na2SO4 and evaporation under reduced pressure
- 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
Reaction notes
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