Sodium Chloride → 2,4-Bis[(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-6-chloro-s-triazine

HRID 1456841Notes

Reaction equation

HRID 1456841 reaction equation
[C:1]([O:5]O)([CH3:4])([CH3:3])C.[Cl-].[Na+].[Cl:9][C:10]1[N:15]=[C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]2[CH2:26][C:25]([CH3:28])([CH3:27])[NH:24][C:23]([CH3:30])([CH3:29])[CH2:22]2)[N:13]=[C:12]([NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH:36]2[CH2:41][C:40]([CH3:43])([CH3:42])[NH:39][C:38]([CH3:45])([CH3:44])[CH2:37]2)[N:11]=1>[Mo](=O)(=O)=O.C1CCCCC1>[Cl:9][C:10]1[N:15]=[C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]2[CH2:26][C:25]([CH3:28])([CH3:27])[N:24]([O:5][CH:1]3[CH2:4][CH2:19][CH2:18][CH2:17][CH2:3]3)[C:23]([CH3:30])([CH3:29])[CH2:22]2)[N:13]=[C:12]([NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH:36]2[CH2:41][C:40]([CH3:43])([CH3:42])[N:39]([O:5][CH:1]3[CH2:4][CH2:22][CH2:21][CH2:20][CH2:3]3)[C:38]([CH3:45])([CH3:44])[CH2:37]2)[N:11]=1

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 6410tert-Butyl hydroperoxideHCID 190733162-chloro-4,6-bis[N-(2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazine

Product 1

HCID 225076382,4-Bis[(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-6-chloro-s-triazineYield 74%

Reagents, catalysts & solvents 2

HCID 14802Molybdenum trioxideCatalystHCID 8078CyclohexaneSolvent

Procedure

A mixture of 57.7 g (0.448 mol) of 70% aqueous tert-butylhydroperoxide, 250 ml of cyclohexane and 100 ml of saturated sodium chloride solution is agitated vigorously and the organic layer is then separated and dried over anhydrous magnesium sulfate. The drying agent is removed by filtration. The filtrate, 30.0 g (0.056 mol) of 2-chloro-4,6-bis[N-(2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazine and 1.0 g of molybdenum trioxide are placed in a pressure bottle and heated at 130°-140° C. The reaction mixture quickly turns red and heating is continued till the red color is discharged. The reaction mixture is allowed to cool and solids are removed by filtration. The filtrate is concentrated under reduced pressure to give an oil which is purified by flash chromatography on silica gel to afford 30.3 g. (74% yield) of the title compound as a white glass.

Workup

  1. customthe organic layer is then separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe drying agent is removed by filtration
  4. temperatureheated at 130°-140° C
  5. temperatureThe reaction mixture quickly turns red and heating
  6. temperatureto cool
  7. customsolids are removed by filtration
  8. concentrationThe filtrate is concentrated under reduced pressure
  9. customto give an oil which
  10. customis purified by flash chromatography on silica gel
  11. customto afford 30.3 g

Sources & evidence

ORD record
ord-0e2e04efba8e4a5cb0ca8a00885788bc
Source dataset
uspto-grants-1998_12
Patent number
US05844026

Reaction notes

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