1-Methylpiperazine → HCID 22557359, compound

HRID 984046Notes

Reaction equation

HRID 984046 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:17]2[C:22](=[O:23])[NH:21][C:20](=[O:24])[CH:19]=[N:18]2)[CH:5]=[CH:6][C:7]=1[CH:8](Cl)[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1.[CH3:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:17]2[C:22](=[O:23])[NH:21][C:20](=[O:24])[CH:19]=[N:18]2)[CH:5]=[CH:6][C:7]=1[CH:8]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[N:29]1[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 225573573-chloro-4-[chloro(4-chlorophenyl)methyl]phenyl-1,2,4-triazine-3,5(2H,4H)-dione

Product 1

HCID 22557359HCID 22557359, compoundYield 17.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-[3-chloro-4-[chloro(4-chlorophenyl)methyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione (0.015 mol) and 1-methylpiperazine (0.04 mol) in DMF (100 ml) was stirred for 24 hours at 80° C. The solvent was evaporated. MIK was added and azeotroped on the rotary evaporator. The residue was stirred in water, then extracted with CH2Cl2. The separated organic layer was washed with water, dried, filtered and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/THF 90/5/5 and CH2Cl2/CH3OH 90/10). The pure fractions were collected and the solvent was evaporated. The residue was stirred overnight in DIPE, then the solvent was evaporated. The residue was crystallized from EtOAc. The precipitate was filtered off, washed with EtOAc, DIPE, then dried, yielding 1.19 g (±)-2-[3-chloro-4-[(4-chlorophenyl)(4-methyl-1-piperazinyl)methyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione (compound 118).

Workup

  1. customThe solvent was evaporated
  2. additionMIK was added
  3. customazeotroped on the rotary evaporator
  4. stirringThe residue was stirred in water
  5. extractionextracted with CH2Cl2
  6. washThe separated organic layer was washed with water
  7. customdried
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/THF 90/5/5 and CH2Cl2/CH3OH 90/10)
  11. customThe pure fractions were collected
  12. customthe solvent was evaporated
  13. stirringThe residue was stirred overnight in DIPE
  14. customthe solvent was evaporated
  15. customThe residue was crystallized from EtOAc
  16. filtrationThe precipitate was filtered off
  17. washwashed with EtOAc, DIPE
  18. customdried

Sources & evidence

ORD record
ord-edfce3438d8c4c8dbba3b9867260f440
Source dataset
uspto-grants-2005_03
Patent number
US06867207B2

Reaction notes

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