Potassium Carbonate → 4-(4-Bromophenylsulphonyl)-1-[2-(4-fluorophenyl)-2-oxoethyl]piperidine

HRID 411513

반응식

HRID 411513 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.Br[CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)=[O:20].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]2[CH2:16][CH2:15][N:14]([CH2:18][C:19]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[O:20])[CH2:13][CH2:12]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 27610704-(4-Bromobenzenesulfonyl)piperidine

생성물 1

HCID 98894284-(4-Bromophenylsulphonyl)-1-[2-(4-fluorophenyl)-2-oxoethyl]piperidine수율 37.9%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

4-(4-Bromophenylsulphonyl)piperidine (Example 1 Step d, 0.9 g, 0.003 mol) was added to a mixture of 2-bromo-4′-fluoroacetophenone (0.7 g, 0.0033 mol) and potassium carbonate (0.84 g, 0.006 mol) in acetonitrile (5 ml) and the resulting slurry stirred at room temperature for 17 h. The insolubles were removed by filtration and the solvent evaporated to give a gum which was purified by column chromatography (SiO2, CH2Cl2:MeOH 97:3) to give 0.5 g (36% yield) of product as a colourless solid. δH (400 MHz, CDCl3) 1.75-1.90 (2H, m), 2.05-2.13 (2H, m), 2.25-2.40 (2H, m), 2.85-3.00 (1H, m), 3.04-3.20 (2H, m), 3.75-3.85 (2H, m), 7.12 (1H, t, 8 Hz), 7.24 (4H, s), 7.98-8.02 (2H, m).

후처리

  1. customThe insolubles were removed by filtration
  2. customthe solvent evaporated
  3. customto give a gum which
  4. customwas purified by column chromatography (SiO2, CH2Cl2:MeOH 97:3)

출처 및 근거

ORD 기록
ord-afd4547216a94dd6a46cd224acdaf7a0
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559166B1

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