Sodium Iodide → 4-(4-Bromophenylsulphonyl)-1-[2-(2,4-difluorophenyl)ethyl]piperidine

HRID 1836338

反応式

HRID 1836338 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[F:17][C:18]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:19]=1[CH2:20][CH2:21]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC#N>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]2[CH2:16][CH2:15][N:14]([CH2:21][CH2:20][C:19]3[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:18]=3[F:17])[CH2:13][CH2:12]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 27610704-(4-Bromobenzenesulfonyl)piperidineHCID 112989892,4-Difluorophenethyl bromide

生成物 1

HCID 110485124-(4-Bromophenylsulphonyl)-1-[2-(2,4-difluorophenyl)ethyl]piperidine収率 58.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 4-(4-bromophenylsulphonyl)piperidine (7.6 g, 0.025 mol), 2,4-difluorophenethyl bromide (8.3 g, 0.38 mol), potassium carbonate (7.5 g, 0.054 mol) and sodium iodide (5.6 g, 0.037 mol) in CH3CN (70 ml) was heated at reflux under nitrogen for 18 h. The reaction mixture was then concentrated and partitioned between water and EtOAc. The organic phase was washed with brine, dried (Na2SO4) and concentrated. Trituration with hexane gave 6.5 g of product as a colourless solid. δH (360 MHz, CDCl3) 1.55-1.75 (2H, m), 1.95-2.05 (4H, m), 2.45-2.55 (2H, m), 2.70-2.75 (2H, m), 2.85-2.95 (1H, m), 3.05-3.10 (2H, m), 6.70-6.85 (2H, m), 7.10-7.15 (1H, m), 7.72 (4H, s).

後処理

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 18 h
  3. concentrationThe reaction mixture was then concentrated
  4. custompartitioned between water and EtOAc
  5. washThe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-f24e819cbe4249689051c30370095566
出典データセット
uspto-grants-2004_08
特許番号
US06777430B2

関連ノート

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