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

HRID 1836344Notes

Reaction equation

HRID 1836344 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]piperidine

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 2.21-2.26 (2H, m),2.90-2.98 (1H, m), 3.07-3.10 (2H, m), 3.77 (2H, s), 7.42 (2H, d, 8 Hz), 7.56 (2H, t, 8 Hz), 7.65-7.69 (1H, m), 7.86-7.93 (4H, 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

Sources & evidence

ORD record
ord-593bf2da57c544529473b325dea4b94b
Source dataset
uspto-grants-2004_08
Patent number
US06777430B2

Reaction notes

Loading…