Piperazine → 2,4-dimethyl-6-(piperazin-1-yl)-1,2,4-triazine-3,5(2H,4H)-dione

HRID 1917091Notes

Reaction equation

HRID 1917091 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[C:8]1[C:9](=[O:17])[N:10]([CH3:16])[C:11](=[O:15])[N:12]([CH3:14])[N:13]=1.C(N(CC)CC)C.ClCCl>C1(C)C=CC=CC=1>[CH3:14][N:12]1[C:11](=[O:15])[N:10]([CH3:16])[C:9](=[O:17])[C:8]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)=[N:13]1

Participants

6

Reactant 4

HCID 4837PiperazineHCID 6344DichloromethaneHCID 8471TriethylamineHCID 2605636-Bromo-2,4-dimethyl-2,3,4,5-tetrahydro-1,2,4-triazine-3,5-dione

Product 1

HCID 337810652,4-dimethyl-6-(piperazin-1-yl)-1,2,4-triazine-3,5(2H,4H)-dioneYield 79.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

4.75 g (55.15 mmol) of piperazine are placed in the presence of 4.05 g (18.4 mmol) of intermediate 1b in toluene at room temperature for 30 min. 2.8 mL (20.1 mmol) of triethylamine are added and the mixture is heated for 18 h at 110° C. After concentration of the reaction medium, the obtained residue is taken up with dichloromethane and washed with water. After drying on MgSO4, the organic phase is dry concentrated. The obtained residue is purified by flash chromatography (CH2Cl2-MeOH: 60-40). 3.3 g of intermediate 12a is obtained as a white powder (yield: 79%).

Workup

  1. washwashed with water
  2. customAfter drying on MgSO4
  3. customthe organic phase is dry
  4. concentrationconcentrated
  5. customThe obtained residue is purified by flash chromatography (CH2Cl2-MeOH: 60-40)

Sources & evidence

ORD record
ord-7c7773de857c4d83bca4048051377588
Source dataset
uspto-grants-2013_12
Patent number
US08618287B2

Reaction notes

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