Allyl bromide → Ethyl trans-4-allyl-2,5-dimethyl-1-piperazinecarboxylate

HRID 538266

Reaktionsgleichung

Reaktionsgleichung von HRID 538266
[CH3:1][C@H:2]1[CH2:7][NH:6][C@H:5]([CH3:8])[CH2:4][N:3]1[C:9]([O:11][CH2:12][CH3:13])=[O:10].[CH2:14](Br)[CH:15]=[CH2:16].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH2:16]([N:6]1[C@H:5]([CH3:8])[CH2:4][N:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C@@H:2]([CH3:1])[CH2:7]1)[CH:15]=[CH2:14]

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 10340Sodium CarbonateHCID 10607598Ethyl trans-2,5-dimethyl-1-piperazinecarboxylate

Produkt 1

HCID 10823138Ethyl trans-4-allyl-2,5-dimethyl-1-piperazinecarboxylateAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of ethyl trans-2,5-dimethyl-1-piperazinecarboxylate (643 g, 3.45 mol), allyl bromide (328 mL, 3.80 mol), and sodium carbonate (440 g, 4.15 mol) in 2500 mL of acetonitrile was heated at reflux for 1.5 hours. The reaction was cooled to room temperature, filtered, and the solvent removed under vacuum. The residue was dissolved in 4000 mL of dichloromethane and washed with two 500 mL portions of 1 M sodium hydroxide. The dichloromethane solution was dried over magnesium sulfate and the solvent was removed to give 630 g (81%) of ethyl trans-4-allyl-2,5-dimethyl-1-piperazinecarboxylate as an oil.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. filtrationfiltered
  4. customthe solvent removed under vacuum
  5. dissolutionThe residue was dissolved in 4000 mL of dichloromethane
  6. washwashed with two 500 mL portions of 1 M sodium hydroxide
  7. dry with materialThe dichloromethane solution was dried over magnesium sulfate
  8. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-b43049bded6b4709bf76bcaf281c51f6
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865721B2

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