Piperazine → HCID 15481711, compound

HRID 1859006Notes

Reaction equation

HRID 1859006 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]1([CH2:13][N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)[C@H:11]([CH3:12])[O:10]1.[NH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.Cl([O-])(=O)(=O)=O.[Li+]>C(#N)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:10])([C@H:11]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)[CH3:12])[CH2:13][N:14]1[CH:18]=[N:17][CH:16]=[N:15]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 101311911-((2-(2,4-Difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazole, (2R-cis)-HCID 23665649Lithium perchlorate

Product 1

HCID 15481711HCID 15481711, compoundYield 111.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (2R,3S)-2-(2,4-difluorophenyl)-3-methyl-2-(1H-1,2,4-triazol-1-yl)methyloxirane (1.0 g, 4.0 mmol), piperazine (860 mg, 10 mmol) and lithium perchlorate (625 mg, 6 mmol) in acetonitrile (15 ml) was heated under reflux for 48 h. The solvent was removed under reduced pressure, the residue was treated with crushed ice and extracted with ethylacetate (3×30 ml). The combined organic extract was washed with water, brine, dried (Na2SO4) and concentrated to give the title compound as thick viscous gum (1.5 g, 78%). The title compound was also prepared by hydrolysis of 2R,3R-2-(2,4-difluorophenyl)-3-(4-ethoxycarbonylpiperazin-1-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 1 with 2M sodium hydroxide solution.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 h
  3. customThe solvent was removed under reduced pressure
  4. additionthe residue was treated with crushed ice
  5. extractionextracted with ethylacetate (3×30 ml)
  6. extractionThe combined organic extract
  7. washwas washed with water, brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-34f7f67a2d4345f7b72e332db8155c1f
Source dataset
uspto-grants-2000_11
Patent number
US06153616

Reaction notes

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