Piperazine → HCID 20327568, compound

HRID 372452Notes

Reaction equation

HRID 372452 reaction equation
[Cl:1][N:2]1[CH:7]=[N:6][C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[NH+:3]1[O-:12].[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>C(O)(C)C>[ClH:1].[N:13]1([C:7]2[N:2]=[N+:3]([O-:12])[C:4]3[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=3[N:6]=2)[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 20327571HCID 20327571, compound

Product 1

HCID 20327568HCID 20327568, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a slurry of 2-chloro-1,2,4-benzotriazine-1-oxide (12.0 g., 0.066 mol.) in 100 ml. of isopropanol is added 11.4 g. (0.132 mol.) of anhydrous piperazine with cooling under N2. The exothermic reaction is moderated at 35°-40° C. for 15 min., and then stirred 2 hours at 20°-25° C. The orange precipitate is collected by suction and partitioned between chloroform and aqueous sodium carbonate. After drying, the CHCl3 extract is concentrated under vacuum to an oil which is taken up in a boiling mixture of 200 ml. of hexane and 200 ml. benzene. The solution is filtered and concentrated under vacuum, and the residue is dissolved in 150 ml. ethanol and treated with 10 ml. of 10N anhydrous ethanolic-HCl. The yellow crystalline crude hydrochloride (9.2 g.) is recrystallized from methanol and then from aqueous ethanol to give pure 3-(1-piperazinyl)-1,2,4-benzotriazine-1-oxide hydrochloride, m.p. 306°-307° C. (dec.).

Workup

  1. customThe exothermic reaction
  2. customThe orange precipitate is collected by suction
  3. custompartitioned between chloroform and aqueous sodium carbonate
  4. customAfter drying
  5. extractionthe CHCl3 extract
  6. concentrationis concentrated under vacuum to an oil which
  7. additionis taken up in a boiling mixture of 200 ml
  8. filtrationThe solution is filtered
  9. concentrationconcentrated under vacuum
  10. dissolutionthe residue is dissolved in 150 ml
  11. additionethanol and treated with 10 ml
  12. customThe yellow crystalline crude hydrochloride (9.2 g.) is recrystallized from methanol

Sources & evidence

ORD record
ord-a7a288abf8e24c889f091e171d3b5c73
Source dataset
uspto-grants-1978_05
Patent number
US04091098

Reaction notes

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