Sulfuric Acid → HCID 67544841, Verbindung

HRID 2176084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2176084
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8]N)=[CH:4][CH:3]=1.[N:11]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[C:14](=O)[CH2:13][CH2:12]2.S(=O)(=O)(O)O>O1CCOCC1>[CH3:10][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:14]3[CH:15]4[CH2:18][CH2:19][N:11]([CH2:12][C:13]=3[C:4]=2[CH:3]=1)[CH2:17][CH2:16]4

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 64203071-Azabicyclo[3.2.2]nonan-4-one

Produkt 1

HCID 67544841HCID 67544841, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

In a 100 mL round-bottomed flask were combined p-tolylhydrazine hydrochloride (1.58 g, 10 mmol; Aldrich), 1-azabicyclo[3.2.2]nonan-4-one (1.392 g, 10.00 mmol; Example 2A), and concentrated sulfuric acid (5 mL) in dioxane (50 mL). The reaction mixture was heated to 80° C. for 2.5 hours, then cooled to room temperature. The solvent was decanted, and the residue was dissolved in water (20 mL) and basified with solid potassium carbonate to pH ˜12. This solution was extracted with dichloromethane (3×50 mL), and the combined organic phases were dried over magnesium sulfate. After removing the solvent under vacuum, the resulting solid was further purified by silica gel column chromatography eluting with 20% methanol-dichloromethane to supply the title compound: 1H NMR (300 MHz, CDCl3) δ ppm 2.07-1.97 (m, 4H), 2.43 (s, 3H), 2.89 (m, 1H), 3.1 (m, 2H), 3.3 (m, 2H), 4.25 (s, 2H), 6.9 (m, 1H), 7.17 (m, 2H), 76 (br s, 1H); MS (DCI/NH3) m/z 227 (M+H)+.

Aufarbeitung

  1. customIn a 100 mL round-bottomed flask were combined
  2. temperaturecooled to room temperature
  3. customThe solvent was decanted
  4. dissolutionthe residue was dissolved in water (20 mL)
  5. extractionThis solution was extracted with dichloromethane (3×50 mL)
  6. dry with materialthe combined organic phases were dried over magnesium sulfate
  7. customAfter removing the solvent under vacuum
  8. customthe resulting solid was further purified by silica gel column chromatography
  9. washeluting with 20% methanol-dichloromethane to supply the title compound

Quellen und Nachweise

ORD-Eintrag
ord-3a7cb69624a24fb293743d78f2893a61
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09063126B2

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