Piperazine → 2,2'-(Piperazine-1,4-diyl)bis[4,6-bis(morpholin-4-yl)-1,3,5-triazine]

HRID 2372552Notes

Reaction equation

HRID 2372552 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1Cl.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.[OH-:16].[Na+].[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>O>[N:10]1([C:2]2[N:4]=[C:5]([N:10]3[CH2:15][CH2:14][O:16][CH2:12][CH2:11]3)[N:7]=[C:8]([N:18]3[CH2:23][CH2:22][N:21]([C:2]4[N:4]=[C:5]([N:10]5[CH2:15][CH2:14][O:13][CH2:12][CH2:11]5)[N:7]=[C:8]([N:10]5[CH2:15][CH2:14][O:13][CH2:12][CH2:11]5)[N:1]=4)[CH2:20][CH2:19]3)[N:1]=2)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 4837PiperazineHCID 7954Cyanuric chlorideHCID 8083MorpholineHCID 14798Sodium Hydroxide3×

Product 1

HCID 148330622,2'-(Piperazine-1,4-diyl)bis[4,6-bis(morpholin-4-yl)-1,3,5-triazine]

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

All operations are carried out under N2. 0.5 mol of cyanuric chloride is suspended in a mixture of 2000 ml of water and 1000 g of ice, and 1.0 mol of morpholine and 0.5 mol of NaOH as a 10% strength by weight aqueous solution are simultaneously added dropwise. The addition is carried out sufficiently slowly that the pH is between 5 and 10. The mixture is subsequently stirred at 25° C. for a further 30 minutes, and a further 0.5 mol of NaOH as a 10% strength by weight aqueous solution is subsequently added dropwise. The reaction mixture is heated at 80° C. for 90 minutes and cooled to room temperature, and 0.28 mol of piperazine and 0.56 mol of NaOH as 10% strength by weight aqueous solutions are subsequently added dropwise. The mixture is subsequently refluxed for 12 hours and filtered at room temperature with suction, and the residue is washed with water and dried. A finely crystalline, white powder is obtained.

Workup

  1. additionare simultaneously added dropwise
  2. additionThe addition
  3. temperatureThe reaction mixture is heated at 80° C. for 90 minutes
  4. temperaturecooled to room temperature
  5. temperatureThe mixture is subsequently refluxed for 12 hours
  6. filtrationfiltered at room temperature with suction
  7. washthe residue is washed with water
  8. customdried
  9. customA finely crystalline, white powder is obtained

Sources & evidence

ORD record
ord-04f4dc376c0d46ebb16ca03cd64006a3
Source dataset
uspto-grants-1992_03
Patent number
US05099017

Reaction notes

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