Hydrochloric Acid → HCID 12136656, compound

HRID 2416669Notes

Reaction equation

HRID 2416669 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])[CH2:7][CH2:6]1)=[O:4].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCCl>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([C:15]2[CH:14]=[CH:13][C:12]([O:17][CH3:18])=[C:11]([CH:8]3[CH2:9][CH2:10][N:5]([C:3](=[O:4])[C:2]([F:1])([F:19])[F:20])[CH2:6][CH2:7]3)[CH:16]=2)(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 73984-Chlorobenzenesulfonyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 12136658HCID 12136658, compound

Product 1

HCID 12136656HCID 12136656, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2,2,2-trifluoro-1-[4-(2-methoxyphenyl)piperidin-1-yl] ethanone (0.285 g; 1 mmol), prepared as in Example 1 Step 1, and 4-chlorobenzenesulfonyl chloride (0.210 g; 1 mmol) in 1,2-dichloroethane (2 mL) at 0° C. under nitrogen atmosphere was added, in small portions, aluminum chloride (0.134 g; 1 mmol), and the mixture was refluxed for 18 h. After cooling to 0° C. a solution of 2N HCl (2 mL) was added and the mixture was extracted into dichloromethane (20 mL). The organic phase was dried (Na2SO4), concentrated in vacuo and the residue was purified by column chromatography on silica gel (eluting with hexane-ethyl acetate (7:3, v/v) to give 1-{4-[5-(4-chloro-benzenesulfonyl)2-methoxyphenyl]piperidin-1-yl}2,2,2-trifluoro-ethanone (31) as white solid (0.077 g; 17%).

Workup

  1. temperaturethe mixture was refluxed for 18 h
  2. additionwas added
  3. extractionthe mixture was extracted into dichloromethane (20 mL)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customthe residue was purified by column chromatography on silica gel (
  7. washeluting with hexane-ethyl acetate (7:3

Sources & evidence

ORD record
ord-a46b368824794a81948f31879e311814
Source dataset
uspto-grants-2004_11
Patent number
US06825202B2

Reaction notes

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