Hydrochloric Acid → 1-(3-Pyridin-2-yl-1,2,4-thiadiazol-5-yl)piperazine

HRID 2262982Notes

Reaction equation

HRID 2262982 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)[S:9][N:8]=1.Cl.CCCCCC>O1CCCC1.C(OCC)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([N:12]2[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]2)[S:9][N:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 68782158HCID 68782158, compound

Product 1

HCID 687780931-(3-Pyridin-2-yl-1,2,4-thiadiazol-5-yl)piperazine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 4-(3-pyridin-2-yl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxylate (6.35 g, 17.0 mmol) was dissolved in tetrahydrofuran (100 ml), and a solution of 4 N hydrogen chloride in ethyl acetate (50 ml) was added thereto, followed by stirring at room temperature for 5 hours. Hexane (250 ml) was poured to the reaction mixture, and a solid was separated by filtration. The obtained solid was dissolved in an aqueous saturated sodium hydrogen carbonate solution, followed by stirring at room temperature for 2 hours. Water was poured to the reaction mixture, and the resulting solution was extracted with a mixed solution of ethyl acetate/tetrahydrofuran (1:1). The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Hexane was added to the residue, and 2.79 g (67.0%) of the desired product as a solid was separated by filtration.

Workup

  1. customa solid was separated by filtration
  2. dissolutionThe obtained solid was dissolved in an aqueous saturated sodium hydrogen carbonate solution
  3. stirringby stirring at room temperature for 2 hours
  4. additionWater was poured to the reaction mixture
  5. extractionthe resulting solution was extracted with a mixed solution of ethyl acetate/tetrahydrofuran (1:1)
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. additionHexane was added to the residue, and 2.79 g (67.0%) of the desired product as a solid
  10. customwas separated by filtration

Sources & evidence

ORD record
ord-9d04af373dac46e4a36136af01991004
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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