Sulfuric Acid → HCID 67544841, 화합물

HRID 2176084노트

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HRID 2176084 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 67544841HCID 67544841, 화합물

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-3a7cb69624a24fb293743d78f2893a61
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09063126B2

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