Sulfuric Acid → HCID 67544841, compound

HRID 2176084Notes

Reaction equation

HRID 2176084 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 67544841HCID 67544841, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-3a7cb69624a24fb293743d78f2893a61
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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