Cyanuric chloride → HCID 20272125, compound

HRID 484939Notes

Reaction equation

HRID 484939 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].[CH3:10][C:11]1([CH3:38])[CH2:16][CH:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:14][C:13]([CH3:37])([CH3:36])[NH:12]1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C(C)=CC=CC=1>[Cl:3][C:2]1[N:1]=[C:8]([N:17]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:15]2[CH2:14][C:13]([CH3:37])([CH3:36])[NH:12][C:11]([CH3:38])([CH3:10])[CH2:16]2)[N:7]=[C:5]([N:17]([CH:15]2[CH2:16][C:11]([CH3:38])([CH3:10])[NH:12][C:13]([CH3:36])([CH3:37])[CH2:14]2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[N:4]=1

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 11430Potassium CarbonateHCID 20133731HCID 20133731, compound

Product 1

HCID 20272125HCID 20272125, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

A solution of 12.0 g of cyanuric chloride in 100 ml of xylene was added dropwise at 20°-25° C. to a solution of 54.0 g of 2,2,6,6-tetramethyl-4-(octadecylamino)piperidine in 200 ml of xylene. The resulting mixture was then heated under reflux for 8 hours, after which it was neutralised with an aqueous solution of potassium carbonate and then extracted with benzene. The extract was dried over anhydrous potassium carbonate and then the solvent was distilled off. The resulting residue was purified by column chromatography through silica gel, eluted with a 20:1:1 by volume mixture of ethyl acetate, ethanol and triethylamine, to give the title compound in the form of crystals. These were recrystallised from ethyl acetate, giving the purified title compound in the form of colourless crystals melting at 68°-70° C.

Workup

  1. temperatureThe resulting mixture was then heated
  2. temperatureunder reflux for 8 hours
  3. extractionextracted with benzene
  4. dry with materialThe extract was dried over anhydrous potassium carbonate
  5. distillationthe solvent was distilled off
  6. customThe resulting residue was purified by column chromatography through silica gel
  7. washeluted with a 20:1:1 by volume mixture of ethyl acetate, ethanol and triethylamine

Sources & evidence

ORD record
ord-af62fb95e88a431f8df81ab145e0a864
Source dataset
uspto-grants-1985_08
Patent number
US04533688

Reaction notes

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