Hydrochloric Acid → 1-Cyclobutylpiperazine

HRID 16825Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 16825
[CH:1]1([N:5]2[CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.Cl>C(OCC)(=O)C.CO.O1CCOCC1>[CH:1]1([N:5]2[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Komponenten

6

Edukt 2

HCID 313Hydrochloric Acid2×HCID 57423951Tert-butyl 4-cyclobutylpiperazine-1-carboxylate

Produkt 1

HCID 47386021-CyclobutylpiperazineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

A solution of tert-butyl 4-cyclobutylpiperazine-1-carboxylate (1.1553 g, 4.81 mmol) in ethyl acetate (10 mL) and methanol (10.00 mL) was treated with a 4M-solution hydrogen chloride in dioxane (1.669 mL, 48.07 mmol) was stirred at room temperature for 40 h under nitrogen. The reaction was incomplete so f 4M-solution hydrogen chloride in dioxane (10 mL) was added and the solution was stirred at room temperature for a further 2 h. The reaction mixture was evaporated to dryness to afford a solid. The crude product was purified by ion exchange chromatography, using a SCX column. The desired product was eluted from the column using 3.5M NH3/MeOH and pure fractions were evaporated to dryness to afford 1-cyclobutylpiperazine (0.571 g, 85%) as a yellow oil.

Aufarbeitung

  1. additionwas added
  2. stirringthe solution was stirred at room temperature for a further 2 h
  3. customThe reaction mixture was evaporated to dryness
  4. customto afford a solid
  5. customThe crude product was purified by ion exchange chromatography
  6. washThe desired product was eluted from the column
  7. customwere evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-50c919d8e3c1402a8e50a89d94f5007d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737149B2

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