Carbon Dioxide → 1-{4-[4-(2-Chloro-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanone

HRID 736127Notes

Reaction equation

HRID 736127 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.C(=O)=O.[F:30][C:31]1[CH:32]=[C:33]([C:43](=[O:45])[CH3:44])[CH:34]=[CH:35][C:36]=1[N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([N:40]1[CH2:39][CH2:38][N:37]([C:36]2[CH:35]=[CH:34][C:33]([C:43](=[O:45])[CH3:44])=[CH:32][C:31]=2[F:30])[CH2:42][CH2:41]1)=[O:6]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 682631,1'-CarbonyldiimidazoleHCID 6856101-(3-Fluoro-4-piperazin-1-ylphenyl)ethanoneHCID 23291322-Chloro-5-(methylsulphonyl)benzoic acid

Product 1

HCID 597937161-{4-[4-(2-Chloro-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanoneYield 49.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-Chloro-5-methanesulfonyl-benzoic acid (200 mg, 0.852 mmol) in DMF (3 ml) was added dropwise 1,1′-Carbonyldiimidazole (142 mg, 0.852 mmol). When the CO2 evolution ceased, the mixture was heated to 50° C. for 15 minutes. The mixture was cooled to room temperature. 1-(3-Fluoro-4-piperazin-1-yl-phenyl)-ethanone (189 mg, 0.852 mmol) was added portionwise. The mixture was stirred at room temperature for 1 hour. The solvent was removed in vacuo. The residue was dissolved in ethyl acetate. The solution was washed twice with water, dried over Na2SO4, filtered and the solvent was removed in vacuo. The crude oil was purified on silica gel (Heptane/AcOEt 0%-50% (15 minutes) to provide the title compound (185 mg, 49%) as a white solid, MS (m/e): 439.1 (M+H+, 100%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washThe solution was washed twice with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customThe crude oil was purified on silica gel (Heptane/AcOEt 0%-50% (15 minutes)

Sources & evidence

ORD record
ord-a61b95f76c8344c18c8797e2ad0e3086
Source dataset
uspto-grants-2009_09
Patent number
US07595314B2

Reaction notes

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