Piperazine → 7-Methyl-3-(1-piperazinyl)-1,2-benzisoxazole

HRID 1032286Notes

Reaction equation

HRID 1032286 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([CH3:17])[C:11]=2[O:10][N:9]=1>C(O)CCC>[CH3:17][C:16]1[C:11]2[O:10][N:9]=[C:8]([N:1]3[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]3)[C:12]=2[CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 150574483-Chloro-7-methylbenzo[d]isoxazole

Product 1

HCID 150574497-Methyl-3-(1-piperazinyl)-1,2-benzisoxazoleYield 71.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a stirred and heated (90° C.) mixture of 120 parts of piperazine and 400 parts of 1-butanol were added dropwise 60 parts of 3-chloro-7-methyl-1,2-benzisoxazole. Upon complete addition, stirring was continued for 6 hours at reflux temperature. After cooling, the reaction mixture was filtered and the filtrate was evaporated. The residue was taken up in water and the product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was solidified on standing, yielding 56 parts (71.5%) of 7-methyl-3-(1-piperazinyl)-1,2-benzisoxazole as a residue (int. 2).

Workup

  1. temperatureheated
  2. additionUpon complete addition
  3. stirringstirring
  4. temperatureat reflux temperature
  5. temperatureAfter cooling
  6. filtrationthe reaction mixture was filtered
  7. customthe filtrate was evaporated
  8. extractionthe product was extracted with trichloromethane
  9. customThe extract was dried
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was purified by column chromatography over silica gel using
  13. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  14. customThe pure fractions were collected
  15. customthe eluent was evaporated

Sources & evidence

ORD record
ord-278517e763474f28aee1f7ff0e1ab8f3
Source dataset
uspto-grants-1990_09
Patent number
US04957916

Reaction notes

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