1-(Methylsulfonyl)piperazine → HCID 53910970, compound

HRID 1859015Notes

Reaction equation

HRID 1859015 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.[CH3:19][S:20]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)(=[O:22])=[O:21]>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:26]1[CH2:27][CH2:28][N:23]([S:20]([CH3:19])(=[O:22])=[O:21])[CH2:24][CH2:25]1)[CH3:12])[CH2:13][N:14]1[CH:18]=[N:17][CH:16]=[N:15]1

Participants

4

Reactant 2

HCID 7091611-(Methylsulfonyl)piperazineHCID 101311911-((2-(2,4-Difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazole, (2R-cis)-

Product 1

HCID 53910970HCID 53910970, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The epoxide IV (300 mg, 1.19 mmol) and LiClO4 (235 mg, 1.43 mmol) were dissolved in 12 mL dry acetonitrile and 1-methanesulfonylpiperazine (190 mg, 1.79 mmol) was added. The mixture was heated to reflux for 4 days, cooled and the solvent evaporated. The residue was dissolved in dichloromethane and then washed with water and brine. The solution was dried over Na2SO4 and the solvent evaporated. The crude reaction products were eluted through a silica gel column using 3% MeOH/97% EtOAc as eluent to give the title compound (180 mg, 36%) as a colorless solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 days
  3. temperaturecooled
  4. customthe solvent evaporated
  5. dissolutionThe residue was dissolved in dichloromethane
  6. washwashed with water and brine
  7. dry with materialThe solution was dried over Na2SO4
  8. customthe solvent evaporated
  9. customThe crude reaction products
  10. washwere eluted through a silica gel column

Sources & evidence

ORD record
ord-d890d4f8f8ac48a6a5a1f99f3d28b135
Source dataset
uspto-grants-2000_11
Patent number
US06153616

Reaction notes

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