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

HRID 408811ノート

反応式

HRID 408811 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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 mmol), 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).

後処理

  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

出典と根拠

ORDレコード
ord-0dfcf06e429a4a50a9c6d75fed7116d8
出典データセット
uspto-grants-2014_06
特許番号
US08759360B2

反応ノート

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