1-Methylpiperazine → HCID 10091734, compound

HRID 981168Notes

Reaction equation

HRID 981168 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
  10. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-0c1760708e5c42798de49456d6296677
Source dataset
uspto-grants-1991_02
Patent number
US04990507

Reaction notes

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