Hydrochloric Acid → N-{1-[2-(6-Methyl-2-pyridyl)ethyl]-4-piperidyl}-4-(N-methylamino)benzenesulfonamide

HRID 260888

反応式

HRID 260888 の反応式
C(O)(=O)C.[NH:5]1[CH2:10][CH2:9][CH:8]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([N:21]([C:23](=O)C)C)=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:7][CH2:6]1.[CH3:26][C:27]1[N:32]=[C:31]([CH:33]=[CH2:34])[CH:30]=[CH:29][CH:28]=1.C([O-])(=O)C.[Na+].[OH-].[Na+].Cl.C(=O)([O-])O.[Na+]>CO.O>[CH3:26][C:27]1[N:32]=[C:31]([CH2:33][CH2:34][N:5]2[CH2:6][CH2:7][CH:8]([NH:11][S:12]([C:15]3[CH:16]=[CH:17][C:18]([NH:21][CH3:23])=[CH:19][CH:20]=3)(=[O:13])=[O:14])[CH2:9][CH2:10]2)[CH:30]=[CH:29][CH:28]=1

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 707352-Ethenyl-6-methylpyridineHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 67690431N-(4-piperidyl)-4-(N-acetyl-N-methylamino)benzenesulfonamide acetate

生成物 1

HCID 22918936N-{1-[2-(6-Methyl-2-pyridyl)ethyl]-4-piperidyl}-4-(N-methylamino)benzenesulfonamide収率 70%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

The N-(4-piperidyl)-4-(N-acetyl-N-methylamino)benzenesulfonamide acetate (3.71 g, 10.0 mmol), 6-methyl-2-vinylpyridine (1.43 g, 12.0 mmol ) and sodium acetate (0.82 g) were dissolved in a mixture comprising methanol (20 ml) and water (20 ml). The obtained solution was heated under reflux for 5 hours, followed by the addition of sodium hydroxide (3.20 g). The obtained mixture was heated under reflux for additional three hours and acidified with 2N aqueous hydrochloric acid. The pH of the mixture was adjusted to about 8 with an aqueous solution of sodium hydrogencarbonate. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of common salt, dried over magnesium sulfate and concentrated. The obtained oily residue was purified by column chromatography (chloroform:methanol:aqueous ammonia=90:9:1) and recrystallized from ethyl acetate/ether to give the title compound as a white crystal (2.71 g, overall yield of two steps: 70%).

後処理

  1. temperatureThe obtained solution was heated
  2. temperatureunder reflux for 5 hours
  3. temperatureThe obtained mixture was heated
  4. temperatureunder reflux for additional three hours
  5. extractionThe resulting mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materiala saturated aqueous solution of common salt, dried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe obtained oily residue was purified by column chromatography (chloroform:methanol:aqueous ammonia=90:9:1)
  10. customrecrystallized from ethyl acetate/ether

出典と根拠

ORDレコード
ord-294fab5ed92d412db7185d88c060a66a
出典データセット
uspto-grants-1996_06
特許番号
US05530118

関連ノート

読み込み中…