Potassium Carbonate → HCID 68107086, compound

HRID 2403571Notes

Reaction equation

HRID 2403571 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[N:12]1(C(OC(C)(C)C)=O)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[ClH:1].[ClH:1].[F:9][C:8]([F:11])([F:10])[C:7]1[C:2]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5898332-Chloro-3-(trifluoromethyl)pyridine

Product 1

HCID 68107086HCID 68107086, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-Chloro-3-(trifluoromethyl)pyridine (1.07 g) and tert-butyl piperazine-1-carboxylate (1.0 g) was dissolved in DMF (10 ml), and K2CO3 (3.0 g) was added thereto, followed by stirring at 80° C. overnight. The reaction mixture was concentrated under reduced pressure, and then a saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with CHCl3. The organic layer was dried over Na2SO4 and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc). The product was dissolved in MeOH (16 ml), and 4 M hydrogen chloride/EtOAc (8 ml) was added thereto, followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure, then EtOAc was added thereto, and the solid was collected by filtration to obtain 1-[3-(trifluoromethyl)pyridin-2-yl]piperazine dihydrochloride (858 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona saturated aqueous sodium hydrogen carbonate solution was added
  3. extractionfollowed by extraction with CHCl3
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationthe solvent was concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)
  7. dissolutionThe product was dissolved in MeOH (16 ml)
  8. addition4 M hydrogen chloride/EtOAc (8 ml) was added
  9. stirringby stirring at room temperature overnight
  10. concentrationThe reaction mixture was concentrated under reduced pressure
  11. additionEtOAc was added
  12. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-65f4ddc39d234ee9afe70258bab9ee4d
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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