Sulfuric Acid → HCID 67545475, compound

HRID 2176117Notes

Reaction equation

HRID 2176117 reaction equation
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8]N)=[CH:4][CH:3]=1.Cl.[CH:12]12[NH:20][CH:16]([CH2:17][CH2:18][CH2:19]1)[CH2:15][C:14](=O)[CH2:13]2.S(=O)(=O)(O)O>O1CCOCC1>[CH3:10][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:8][C:14]1[CH2:13][CH:12]3[NH:20][CH:16]([C:15]2=1)[CH2:17][CH2:18][CH2:19]3

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 197915239-Azabicyclo[3.3.1]nonan-3-one--hydrogen chloride (1/1)

Product 1

HCID 67545475HCID 67545475, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

In a 100 mL round-bottom flask were combined p-tolylhydrazine hydrochloride (1.80 g, 11.4 mmol; Alfa Aesar), 9-azabicyclo[3.3.1]nonan-3-one hydrochloride (2.0 g, 11.4 mmol; Accela ChemBio), 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 residue was purified by silica gel chromatography (CH2Cl2/CH3OH, 3:1) to afford the title compound: 1H NMR (300 MHz, CDCl3) δ ppm 1.39-1.50 (m, 2H), 1.75 (d, J=14 Hz, 2H), 1.91-2.07 (m, 2H), 2.38 (s, 3H), 2.72 (d, J=17 Hz, 1H), 3.27-3.39 (m, 1H), 3.70 (t, J=5 Hz, 1H), 4.55 (t, J=3 Hz, 1H), 6.88 (dd, J=8, 1 Hz, 1H), 7.14 (s, 1H), 7.18 (d, J=8 Hz, 1H); MS (DCI/NH3) m/z 227 (M+H)+.

Workup

  1. customIn a 100 mL round-bottom 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 residue was purified by silica gel chromatography (CH2Cl2/CH3OH, 3:1)

Sources & evidence

ORD record
ord-4a2d2b27c1004943884df25608a319d4
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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