1-Methylpiperazine → HCID 178480777, compound

HRID 437121Notes

Reaction equation

HRID 437121 reaction equation
[N+](C1C=C(S(O[C:14]2[NH:15][S:16](=[O:25])(=[O:24])[C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)(=O)=O)C=CC=1)([O-])=O.[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>CC(C)=O>[CH3:26][N:27]1[CH2:32][CH2:31][N:30]([C:14]2[NH:15][S:16](=[O:24])(=[O:25])[C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 178526645HCID 178526645, compound

Product 1

HCID 178480777HCID 178480777, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred suspension of 1.0 g of 3-(m-nitrobenzenesulfonyloxy)-2H-1,2,4-benzothiadiazine 1,1-dioxide in 10 ml of acetone is added dropwise 0.53 g of 1-methylpiperazine, while the mixture is cooled in an ice bath. After the addition, the mixture is stirred at room temperature for 1 hour. After removal of acetone by distillation under reduced pressure, 30 ml of water is added to the residue. The crystalline precipitate is collected by suction filtration and treated with 2 ml of a 10% aqueous sodium hydroxide solution. After removal of the insoluble materials by suction filtration, the filtrate is adjusted to a pH 8.0 with dilute hydrochloric acid. The crystalline precipitate is collected by suction filtration and recrystallized from a mixture of dimethylformamide and water to give 0.2 g of the desired product, m.p. 265°-267° C.

Workup

  1. temperaturewhile the mixture is cooled in an ice bath
  2. additionAfter the addition
  3. customAfter removal of acetone
  4. distillationby distillation under reduced pressure, 30 ml of water
  5. additionis added to the residue
  6. filtrationThe crystalline precipitate is collected by suction filtration
  7. additiontreated with 2 ml of a 10% aqueous sodium hydroxide solution
  8. customAfter removal of the insoluble materials
  9. filtrationby suction filtration
  10. filtrationThe crystalline precipitate is collected by suction filtration
  11. customrecrystallized from a mixture of dimethylformamide and water

Sources & evidence

ORD record
ord-a626a82bc33141628f33c8ff0e05b8aa
Source dataset
uspto-grants-1977_06
Patent number
US04029780

Reaction notes

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