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

HRID 411513Notes

Reaction equation

HRID 411513 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-afd4547216a94dd6a46cd224acdaf7a0
Source dataset
uspto-grants-2003_05
Patent number
US06559166B1

Reaction notes

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