Hydrogen Peroxide → 8-Benzyl-2,3,8-triaza-spiro[4.5]dec-2-ene

HRID 1024365Notes

Reaction equation

HRID 1024365 reaction equation
[NH2:1][CH2:2][C:3]1([CH2:16][NH2:17])[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:4]1.CO.OO.[O-]Cl.[Na+]>O>[CH2:9]([N:6]1[CH2:5][CH2:4][C:3]2([CH2:2][N:1]=[N:17][CH2:16]2)[CH2:8][CH2:7]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 12326861(1-Benzylpiperidine-4,4-diyl)dimethanamineHCID 23665760Sodium Hypochlorite

Product 1

HCID 565940618-Benzyl-2,3,8-triaza-spiro[4.5]dec-2-eneYield 90.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.48 g of C-(4-Aminomethyl-1-benzyl-piperidin-4-yl)-methylamine was suspended in 40 mL H2O and 10 mL MeOH and cooled with an ice bath. Simultaneously, 6.7 mL 30% H2O2 (6 equiv.) and 15.2 mL 10% NaClO (2.4 equiv.) were added dropwise. The mixture was stirred at room temperature for 1 hour. The mixture was extracted 2 times with DCM, the combined organic layers were dried over Na2SO4, filtrated and concentrated to yield 2.20 g of a yellow oil which was used without further purification in the subsequent step.

Workup

  1. extractionThe mixture was extracted 2 times with DCM
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. filtrationfiltrated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3d38630b0d6044e0993a671856066298
Source dataset
uspto-grants-2014_05
Patent number
US08722887B2

Reaction notes

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