Hydrochloric Acid → 1-Benzyl-4-(4-methoxyphenyl)-1,2,3,6-tetrahydropyridine

HRID 1411400ノート

反応式

HRID 1411400 の反応式
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][C:12]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)(O)[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>O1CCOCC1>[CH2:2]([N:9]1[CH2:10][CH:11]=[C:12]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[CH2:13][CH2:14]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 159073291-Benzyl-4-(4-methoxyphenyl)piperidin-4-ol

生成物 1

HCID 106364031-Benzyl-4-(4-methoxyphenyl)-1,2,3,6-tetrahydropyridine収率 53.7%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

6 M HCl (100 mL, aqueous) was added to a solution of 1-benzyl-4-(4-methoxyphenyl)piperidin-4-ol (12.31 g, 41.36 mmol) in dioxane (50 mL), and the reaction was heated to strong reflux (110° C.). After 2 hours, the reaction was not complete. The heat was turned off and the reaction was left to stir at ambient temperature for 2 days. The reaction had progressed but was not complete so it was heated to 110° C. After 1 hour, the reaction was cooled and the volume was reduced by approximately one third. The solution was then cooled in an ice bath and neutralized with NaOH pellets. The thick suspension was filtered. The precipitate was rinsed with water and then dried under vacuum at 70° C. to afford 6.2 g (47%) of the titled compound. 1H NMR (400 MHz, CDCl3) δ ppm 2.74-2.62 (m, 1H), 3.30-3.06 (m, 2H), 3.50 (d, J=18.5, 1H), 3.67-3.56 (m, 1H), 3.82 (s, 3H), 4.03-3.90 (m, 1H), 4.21 (dd, J=5.7, 13.0, 1H), 4.34 (dd, J=5.1, 13.0, 1H), 5.88 (s, 1H), 6.88 (d, J=8.7, 2H), 7.32 (d, J=8.7, 2H), 7.51-7.43 (m, 3H), 7.71 (dd, J=2.7, 6.3, 2H), 12.85 (s, 1H); MS (ESI) m/z 280 (M+H)+; MS (DCI) m/z 280 (M+H)+.

後処理

  1. temperaturethe reaction was heated
  2. waitthe reaction was left
  3. temperaturewas heated to 110° C
  4. waitAfter 1 hour
  5. temperaturethe reaction was cooled
  6. temperatureThe solution was then cooled in an ice bath
  7. filtrationThe thick suspension was filtered
  8. washThe precipitate was rinsed with water
  9. customdried under vacuum at 70° C.

出典と根拠

ORDレコード
ord-cff3286e35854327b4b79c608b779d81
出典データセット
uspto-grants-2014_12
特許番号
US08921514B2

反応ノート

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