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

HRID 1351909Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1351909
[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, VerbindungAusbeute 11 %

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 g) 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-14a3cf1a75444593bdbd099c522bf0cd
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07217706B2

Notizen zur Reaktion

Wird geladen…