Sulfuric Acid → HCID 67544841、化合物

HRID 2176084ノート

反応式

HRID 2176084 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 67544841HCID 67544841、化合物

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-3a7cb69624a24fb293743d78f2893a61
出典データセット
uspto-grants-2015_06
特許番号
US09063126B2

反応ノート

読み込み中…