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

HRID 1820803Notes

Reaction equation

HRID 1820803 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-36a197bf4540430a93644123cddf2a06
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

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