Hydrochloric Acid → 1-(4-Cyclobutanesulfonyl-2-fluoro-phenyl)-piperazine hydrochloride

HRID 2251258Notes

Reaction equation

HRID 2251258 reaction equation
[CH:1]1([S:5]([C:8]2[CH:13]=[CH:12][C:11](F)=[C:10]([F:15])[CH:9]=2)(=[O:7])=[O:6])[CH2:4][CH2:3][CH2:2]1.[NH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.[ClH:22]>CN(C)C(=O)C.O1CCOCC1>[ClH:22].[CH:1]1([S:5]([C:8]2[CH:13]=[CH:12][C:11]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[C:10]([F:15])[CH:9]=2)(=[O:7])=[O:6])[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4837PiperazineHCID 69036720HCID 69036720, compound

Product 1

HCID 690360641-(4-Cyclobutanesulfonyl-2-fluoro-phenyl)-piperazine hydrochloride

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

To 2.8 mmol 4-cyclobutanesulfonyl-1,2-difluoro-benzene in 20 ml N,N-dimethylacetamide was added 8.3 mmol piperazine, and the mixture was heated at 80° C. for 45 min. The mixture was then concentrated in vacuo, and the residue was chromatographed on silica gel (eluant: ethyl acetate/methanol gradient). The product-containing fractions were combined and concentrated in vacuo. The residue was resuspended in 100 ml dioxane, and 6.0 mmol HCl (as a 4 M solution in dioxane) was added. After stirring for 10 min, the ensuing white crystals were collected by filtration, washing twice with ether, to afford the title compound.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customthe residue was chromatographed on silica gel (eluant: ethyl acetate/methanol gradient)
  3. concentrationconcentrated in vacuo
  4. filtrationthe ensuing white crystals were collected by filtration
  5. washwashing twice with ether

Sources & evidence

ORD record
ord-60919453a5ea429fb90cd6db0dc80fb6
Source dataset
uspto-grants-2008_01
Patent number
US07319099B2

Reaction notes

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