Piperazine → HCID 13393693, compound

HRID 1589636Notes

Reaction equation

HRID 1589636 reaction equation
[CH3:1][C:2]1[N:7]=[C:6](SC)[N:5]2[CH:10]=[N:11][N:12]=[C:4]2[CH:3]=1.[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.O1CCOCC1>O.C(Cl)(Cl)Cl>[CH3:1][C:2]1[N:7]=[C:6]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[N:12]2[N:11]=[CH:10][N:5]=[C:4]2[CH:3]=1

Participants

6

Reactant 3

HCID 4837PiperazineHCID 312751,4-DioxaneHCID 12581790HCID 12581790, compound

Product 1

HCID 13393693HCID 13393693, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 6.00 g (33.3 mmole) of 7-methyl-5-methylthio-1,2,4-triazolo[4,3-c]pyrimidine, 30.0 g (0.35 mmole) of piperazine and 250 ml of dioxane was refluxed under nitrogen for six days. The mixture was cooled and concentrated in vacuo. The residue obtained was dissolved in 150 ml of water, and the solution was extracted four times with 150 ml portions of chloroform. The extracts were washed thrice with 150 ml portions of water and twice with 150 ml portions of sodium chloride solution and were dried over magnesium sulfate. Evaporation provided a yellow solid which was taken up in 150 ml of chloroform, filtered and chromatographed on a high pressure liquid chromatograph, eluting with methanol-ethyl acetate (1:1). Infrared and nuclear magnetic resonance spectral analyses showed fractions 2 and 3 to be 7-methyl-5-(1-piperazino)-1,2,4-triazolo-[1,5-c]pyrimidine, m.p. 92-95 C. Analysis: Calculated for C10H14N6 : %C, 55.0; %H, 6.5; %N, 38.5; Found: %C, 54.8; %H, 6.4; %N, 38.3. Fraction 4 contained about 15% of 7-methyl-5-(1-piperazino)-1,2,4-triazolo[4,3-c]pyrimidine.

Workup

  1. temperaturewas refluxed under nitrogen for six days
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated in vacuo
  4. customThe residue obtained
  5. extractionthe solution was extracted four times with 150 ml portions of chloroform
  6. washThe extracts were washed thrice with 150 ml portions of water
  7. dry with materialtwice with 150 ml portions of sodium chloride solution and were dried over magnesium sulfate
  8. customEvaporation
  9. customprovided a yellow solid which
  10. filtrationfiltered
  11. customchromatographed on a high pressure liquid chromatograph
  12. washeluting with methanol-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-a7232a76548d400f8eef6b0f211269fe
Source dataset
uspto-grants-1986_02
Patent number
US04572910

Reaction notes

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