Cyanuric chloride → HCID 19832528, compound

HRID 2051579Notes

Reaction equation

HRID 2051579 reaction equation
[CH:1]1([O:7][N:8]2[C:13]([CH3:15])([CH3:14])[CH2:12][CH:11]([OH:16])[CH2:10][C:9]2([CH3:18])[CH3:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[N:21]1[C:28](Cl)=[N:27][C:25](Cl)=[N:24][C:22]=1Cl>CS(C)=O.O1CCOCC1>[CH:1]1([O:7][N:8]2[C:9]([CH3:18])([CH3:17])[CH2:10][CH:11]([O:16][C:22]3[N:24]=[C:25]([O:16][CH:11]4[CH2:10][C:9]([CH3:18])([CH3:17])[N:8]([O:7][CH:1]5[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]5)[C:13]([CH3:14])([CH3:15])[CH2:12]4)[N:27]=[C:28]([O:16][CH:11]4[CH2:12][C:13]([CH3:14])([CH3:15])[N:8]([O:7][CH:1]5[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]5)[C:9]([CH3:18])([CH3:17])[CH2:10]4)[N:21]=3)[CH2:12][C:13]2([CH3:14])[CH3:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 7954Cyanuric chlorideHCID 24758Sodium hydrideHCID 113228111-Cyclohexyloxy-2,2,6,6-tetramethyl-piperidin-4-ol

Product 1

HCID 19832528HCID 19832528, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideCatalystHCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of 30.0 g (0.117 mol) of 1-cyclohexyloxy-4-hydroxy-2,2,6,6-tetramethylpiperidine, 2.8 g (0.117 mol) of sodium hydride, a few drops of dimethyl sulfoxide, and 150 ml of 1,4-dioxane is heated at reflux for two hours, then allowed to cool. To this mixture is added over 15 minutes solution of 7.2 g (0.039 mol) of cyanuric chloride in 50 ml of dioxane. Salt formation is observed, and the reaction temperature rises from 20° C to 50° C during the addition. The reaction mixture is then heated at reflux for 30 minute and stirred overnight at room temperature. Salts are removed by filtration, and the salt cake is slurried in water and filtered to remove salt from the product, a solid. The crude product is dissolved in boiling methanol and residual salt is removed by filtration. Additional product is recovered from the dioxane filtration. Crude solids are combined and heated in refluxing 2-propanol. Th resulting suspension is allowed to cool, and the solid is isolated by filtration to afford 19.4 g (59% yield) of the title compound, a white solid, m.p. 242°-5° C. (dec.).

Workup

  1. temperatureis heated
  2. temperatureat reflux for two hours
  3. temperatureto cool
  4. additionthe reaction temperature rises from 20° C to 50° C during the addition
  5. temperatureThe reaction mixture is then heated
  6. temperatureat reflux for 30 minute
  7. customSalts are removed by filtration
  8. filtrationfiltered
  9. customto remove salt from the product
  10. dissolutionThe crude product is dissolved
  11. customis removed by filtration
  12. filtrationAdditional product is recovered from the dioxane filtration
  13. temperatureheated
  14. temperaturein refluxing 2-propanol
  15. temperatureto cool
  16. customthe solid is isolated by filtration

Sources & evidence

ORD record
ord-c69ed2e9a6934cf9b59e86cc4452e92c
Source dataset
uspto-grants-1991_05
Patent number
US05019613

Reaction notes

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