Potassium Carbonate → 4-Benzyl-1-[2-(3-nitrobenzenesulfonyl)ethyl]piperidine

HRID 914996ノート

反応式

HRID 914996 の反応式
CS(O[CH2:6][CH2:7][S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1)(=[O:10])=[O:9])(=O)=O.[CH2:20]([CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:20]([CH:27]1[CH2:32][CH2:31][N:30]([CH2:6][CH2:7][S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)(=[O:10])=[O:9])[CH2:29][CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 317384-BenzylpiperidineHCID 589580692-(3-Nitro-benzenesulfonyl)ethyl methanesulfonate

生成物 1

HCID 589580954-Benzyl-1-[2-(3-nitrobenzenesulfonyl)ethyl]piperidine収率 21%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

A mixture of 102 (1.0 g, 3.2 mmol), 4-benzylpiperidine (103) (0.62 g, 3.5 mmol), and potassium carbonate (1.1 g, 8.0 mmol) in acetonitrile (10 ml) was heated at 70° C. overnight. It was allowed to cool to room temperature and partitioned between EtOAc (150 mL) and water (150 mL). The organic layer was washed with water (100 ml), brine (100 ml), dried over MgSO4, and concentrated. The residue was chromatographed on silica gel (8:1 to 4:1 to 2:1 hexanes/EtOAc) to give 104 (0.26 g, 21%).

後処理

  1. temperatureto cool to room temperature
  2. custompartitioned between EtOAc (150 mL) and water (150 mL)
  3. washThe organic layer was washed with water (100 ml), brine (100 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (8:1 to 4:1 to 2:1 hexanes/EtOAc)

出典と根拠

ORDレコード
ord-fe2f3574e2734c1f980f4c895d8bb1a7
出典データセット
uspto-grants-2007_09
特許番号
US07265122B2

反応ノート

読み込み中…