Piperazine → 1-(5-Trifluoromethyl-pyridin-2-yl)-piperazine

HRID 2241884Notes

Reaction equation

HRID 2241884 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]=1>C(#N)C>[F:15][C:14]([F:17])([F:16])[C:11]1[CH:12]=[CH:13][C:8]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 923422-Chloro-5-(trifluoromethyl)pyridine

Product 1

HCID 6676181-(5-Trifluoromethyl-pyridin-2-yl)-piperazineYield 69.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of 7.1 grams (0.083 mole) of piperazine (commercially available) and 5.0 grams (0.028 mole) of 2-chloro-5-(trifluoromethyl)pyridine (commercially available) in 75 mL of acetonitrile was heated at reflux during a two-hour period. After this time the reaction mixture was allowed to cool to ambient temperature, and then it was filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was dissolved in 75 mL of methylene chloride and washed with two 50 mL portions of water. The organic layer was dried with sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using 100% methylene chloride, then 5% methanol in methylene chloride as eluants. The appropriate fractions were combined and concentrated under reduced pressure, yielding 4.5 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureat reflux during a two-hour period
  2. filtrationit was filtered
  3. concentrationThe filtrate was concentrated under reduced pressure to a residue
  4. dissolutionThe residue was dissolved in 75 mL of methylene chloride
  5. washwashed with two 50 mL portions of water
  6. dry with materialThe organic layer was dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure to a residue
  9. customThe residue was purified with column chromatography on silica gel using 100% methylene chloride
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-17a105c3ba3943e6bfa0a542c5422442
Source dataset
uspto-grants-2010_03
Patent number
US07671055B2

Reaction notes

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