Hydrogen Peroxide → HCID 59339474, compound

HRID 1024369

Reaction equation

HRID 1024369 reaction equation
[NH2:1][CH2:2][C:3]1([CH2:9][NH2:10])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.OO.[O-]Cl.[Na+]>O.CO>[CH2:9]1[C:3]2([CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)[CH2:2][N:1]=[N:10]1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 68738[4-(Aminomethyl)oxan-4-yl]methanamineHCID 23665760Sodium Hypochlorite

Product 1

HCID 59339474HCID 59339474, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

C-(4-Aminomethyl-tetrahydro-pyran-4-yl)-methylamine (1.0 g) was taken up in a mixture of H2O (10 mL) and MeOH (2.5 mL), and cooled in an ice bath. Simultaneously, H2O2 (4.8 mL of a 30% solution, 6 equiv.) and NaClO (12.4 mL of a 10% solution, 2.4 equiv.) were added dropwise, the ice bath was removed, and the mixture was stirred overnight at room temperature. Extraction with DCM, drying over Na2SO4 and evaporation under reduced pressure yielded 380 mg of a clear, light-yellow liquid containing 85% of the anticipated product and 15% of the diamine starting material. This material was used in subsequent steps without further purification. 1H NMR (400 MHz, CDCl3) δ 1.49 (t, 4H), 3.65 (t, 4H), 4.28 (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 380 mg of a clear, light-yellow liquid

Sources & evidence

ORD record
ord-2a5a269aa70a42348b20b69165ffa7d2
Source dataset
uspto-grants-2014_05
Patent number
US08722887B2

Linked notes

Loading…