Potassium Carbonate → 2-Chloro-4-(1-acetyl-2,2,6,6-tetramethylpiperidin-4-oxy)-6-(2,2,6,6-tetramethylpiperidin-1-yl)-1,3,5-triazine

HRID 345994Notes

Reaction equation

HRID 345994 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([N:9]2[C:14]([CH3:16])([CH3:15])[CH2:13][CH2:12][CH2:11][C:10]2([CH3:18])[CH3:17])[N:3]=1.[OH-].[K+].C(=O)([O-])[O-].[K+].[K+].[C:27]([N:30]1[C:35]([CH3:37])([CH3:36])[CH2:34][CH:33]([OH:38])[CH2:32][C:31]1([CH3:40])[CH3:39])(=[O:29])[CH3:28]>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:8][C:6]1[N:7]=[C:2]([O:38][CH:33]2[CH2:34][C:35]([CH3:36])([CH3:37])[N:30]([C:27](=[O:29])[CH3:28])[C:31]([CH3:40])([CH3:39])[CH2:32]2)[N:3]=[C:4]([N:9]2[C:14]([CH3:16])([CH3:15])[CH2:13][CH2:12][CH2:11][C:10]2([CH3:18])[CH3:17])[N:5]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 145493121-(4-Hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)ethan-1-oneHCID 199917662,4-Dichloro-6-(2,2,6,6-tetramethylpiperidin-1-yl)-1,3,5-triazine

Product 1

HCID 199917782-Chloro-4-(1-acetyl-2,2,6,6-tetramethylpiperidin-4-oxy)-6-(2,2,6,6-tetramethylpiperidin-1-yl)-1,3,5-triazine

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

43.4 g of 2,4-dichloro-6-(2,2,6,6-tetramethylpiperidin-1-yl)-1,3,5-triazine (product from Example 1) are dissolved in 175 ml of toluene, after which 42.1 g of pulverized KOH, 1 g of potassium carbonate and 3.4 g of tetrabutylammonium hydrogen sulfate are added. A solution of 29.9 g of 1-acetyl-2,2,6,6-tetramethyl-4-hydroxy-piperidine in 110 ml of toluene is then added dropwise, the internal temperature being maintained at 10° using an ice bath. After stirring for 3.5 hours, 100 ml of water are added. The phases are separated, and the organic phase is washed with water, dried over Na2SO4 and evaporated. After recrystallizing from hexane, the above product is produced as a white powder which melts at 114°-116° C.

Workup

  1. temperaturethe internal temperature being maintained at 10°
  2. customThe phases are separated
  3. washthe organic phase is washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customAfter recrystallizing from hexane
  7. customthe above product is produced as a white powder which melts at 114°-116° C.

Sources & evidence

ORD record
ord-9fbad73837c84bddab7d6e029b6b2c74
Source dataset
uspto-grants-1991_10
Patent number
US05059689

Reaction notes

Loading…