StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Tetrahydrofuran → 4-Benzyl-1-(2-oxazol-2-ylphenyl)piperazine

HRID 342547
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 342547
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.C([Li])CCC.F[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1[O:32][CH:33]=[CH:34][N:35]=1>O>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[O:32][CH:33]=[CH:34][N:35]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 759941-BenzylpiperazineHCID 106070862-(2-Fluorophenyl)oxazoleHCID 178418339Butyllithium

Produkt 1

HCID 105676524-Benzyl-1-(2-oxazol-2-ylphenyl)piperazineAusbeute 37,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of N-benzylpiperazine (3.56 g, 20.2 mmol) and THF (25 mL) was cooled to 0° C. and n-butyllithium (2.5M in hexanes, 7.6 mL, 19 mmol) was added. The mixture was cooled 30 minutes with stirring at 0° C., stirred 1 hour at 25° C., then cooled to 0° C. and 2-fluoro-1-oxazol-2-ylbenzene (1.1 g, 6.75 mmol) was added slowly. The reaction mixture was allowed to warm to 25° C., then stirred 90 minutes and diluted with water. The aqueous layer was separated and extracted with ethyl acetate (3×30 mL). The combined extracts were washed with brine, dried (MgSO4) and concentrated. The residue was purified on silica gel by column chromatography eluting with hexanes/ethyl acetate (9:1) to give 4-benzyl-1-(2-oxazol-2-ylphenyl)piperazine (0.805 g, 2.52 mmol).

Aufarbeitung

  1. temperatureThe mixture was cooled 30 minutes
  2. stirringstirred 1 hour at 25° C.
  3. temperaturecooled to 0° C.
  4. temperatureto warm to 25° C.
  5. stirringstirred 90 minutes
  6. customThe aqueous layer was separated
  7. extractionextracted with ethyl acetate (3×30 mL)
  8. washThe combined extracts were washed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customThe residue was purified on silica gel by column chromatography
  12. washeluting with hexanes/ethyl acetate (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-bef7c156cbb044038036b4f035a8d203
Quelldatensatz
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05859014

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion