3-(Oxiran-2-yl)pyridine → HCID 18007277, Verbindung

HRID 2299696Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2299696
[O:1]1[CH2:3][CH:2]1[C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.[CH2:10]([NH:17][CH:18]1[CH2:24][CH2:23][CH2:22][C:21]2[CH:25]=[CH:26][C:27]([O:29][CH3:30])=[CH:28][C:20]=2[CH2:19]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)C>[CH2:10]([N:17]([CH2:3][CH:2]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)[OH:1])[CH:18]1[CH2:24][CH2:23][CH2:22][C:21]2[CH:25]=[CH:26][C:27]([O:29][CH3:30])=[CH:28][C:20]=2[CH2:19]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

4

Edukt 2

HCID 133195613-(Oxiran-2-yl)pyridineHCID 18007303HCID 18007303, Verbindung

Produkt 1

HCID 18007277HCID 18007277, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Under nitrogen, a solution of 3-oxiranylpyridine (1.9 g) and N-benzyl-(3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine (3.3 9) in ethanol (15 ml) was refluxed for 5 hours. After removal of ethanol in vacuo, the residue was dissolved into a mixture of aqueous sodium hydrogencarbonate and ethyl acetate. After separation, the organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (chloroform:methanol=20:1) to give 2-[N-benzyl-N-(3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl) amino]-1-(pyridin-3-yl)ethanol (520 mg).

Aufarbeitung

  1. customAfter removal of ethanol in vacuo
  2. dissolutionthe residue was dissolved into a mixture of aqueous sodium hydrogencarbonate and ethyl acetate
  3. customAfter separation
  4. washthe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-21ab8396476b43d48480b0713040dfc9
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06495546B1

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