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

HRID 888967Notes

Reaction equation

HRID 888967 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+].O1CCOCC1.Br[CH2:29][CH2:30][F:31]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:29][CH2:30][F:31])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 129822-Fluoroethyl bromideHCID 312751,4-DioxaneHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

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

Procedure

Charge a reaction vessel with N-tert-butoxycarbonylpiperazine (8.590 mmoles, 1.600 g), potassium carbonate (25.771 mmoles, 3.562 g), sodium iodide (cat.) (66.714 μmoles, 10.000 mg), 1,4-dioxane (234.262 mmoles, 20.000 mL), 1-bromo-2-fluoroethane (9.449 mmoles, 704.029 μL), and a stirbar. Heat with stirring overnight at reflux. Upon reaction completion, cool to room temperature and concentrate under reduced pressure. Partition 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. GCMS (m/z): 232 (M).

Workup

  1. temperatureHeat
  2. temperatureat reflux
  3. customUpon reaction completion
  4. concentrationconcentrate under reduced pressure
  5. customPartition 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-b44ca8d9870e4de5a0bc725886803f98
Source dataset
uspto-grants-2012_08
Patent number
US08252798B2

Reaction notes

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