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

HRID 411513

反応式

HRID 411513 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.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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-afd4547216a94dd6a46cd224acdaf7a0
出典データセット
uspto-grants-2003_05
特許番号
US06559166B1

関連ノート

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