Sodium Iodide → tert-Butyl 4-(2-fluoroethyl)piperazine-1-carboxylate

HRID 2370064Notes

Reaction equation

HRID 2370064 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH2:23][CH2:24][F:25]>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:23][CH2:24][F:25])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 129822-Fluoroethyl bromideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 21082715tert-Butyl 4-(2-fluoroethyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Charge a reaction vessel with N-tert-butoxycarbonylpiperazine (1.600 g, 8.590 mmol), potassium carbonate (3.56 g, 25.77 mmol), sodium iodide (catalytic) (10 mg, 66.7 μmol), 1,4-dioxane (20 mL), and 1-bromo-2-fluoroethane (704.0 μL 9.45 mmol). Heat the mixture with stirring at reflux temperature overnight. Upon reaction completion, cool to room temperature and concentrate under reduced pressure. Partition the resulting residue with ethyl acetate and water. Separate the organic layer and dry over anhydrous sodium sulfate, filter, and concentrate under reduced pressure to afford pure 4-(2-fluoro-ethyl)-piperazine-1-carboxylic acid tert-butyl ester. GC-MS m/z 232 (M).

Workup

  1. temperatureHeat the mixture
  2. temperatureat reflux temperature overnight
  3. customUpon reaction completion
  4. concentrationconcentrate under reduced pressure
  5. customPartition the resulting residue with ethyl acetate and water
  6. customSeparate the organic layer
  7. dry with materialdry over anhydrous sodium sulfate
  8. filtrationfilter
  9. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-83f0b5fc8cdb4c1ebec6e1f88fcbe011
Source dataset
uspto-grants-2014_04
Patent number
US08710063B2

Reaction notes

Loading…