1-Methylpiperazine → HCID 10091734, compound

HRID 2106825Notes

Reaction equation

HRID 2106825 reaction equation
Br[CH2:2][C:3]1[N:4]=[N:5][C:6]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1.[CH3:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>C(O)(C)C>[CH3:24][N:25]1[CH2:30][CH2:29][N:28]([CH2:2][C:3]2[N:4]=[N:5][C:6]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:7][C:8]=2[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 11726606HCID 11726606, compound

Product 1

HCID 10091734HCID 10091734, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 3-bromomethyl-4-(3-nitrophenyl)-6-phenylpyridazine (0.6 g), 1-methylpiperazine (0.36 g) in isopropyl alcohol (6 ml) was refluxed for 30 minutes. After evaporating the solvent, the residue was dissolved in methylene chloride (50 ml), washed with saturated aqueous sodium chloride and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to a column chromatography on silica gel (50 g) and eluted with a mixture of chloroform and methanol (20:1 V/V). The fractions containing the desired compound were combined and concentrated under reduced pressure The residue was recrystallized from ethanol to give 3-(4-methylpiperazin-1-ylmethyl)-4-(3-nitrophenyl)-6-phenylpyridazine (0.32 g).

Workup

  1. temperaturewas refluxed for 30 minutes
  2. customAfter evaporating the solvent
  3. dissolutionthe residue was dissolved in methylene chloride (50 ml)
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. washeluted with a mixture of chloroform and methanol (20:1 V/V)
  8. additionThe fractions containing the desired compound
  9. concentrationconcentrated under reduced pressure The residue
  10. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-40be541e429e496f96e8eb88241abbdd
Source dataset
uspto-grants-1990_06
Patent number
US04931453

Reaction notes

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