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

HRID 1836338

반응식

HRID 1836338 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f24e819cbe4249689051c30370095566
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06777430B2

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