Sodium Hydroxide → 4-[Bis(4-fluorophenyl)methylene]-1-(phenylsulfonyl)piperidine

HRID 1709809Notes

Reaction equation

HRID 1709809 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)([CH:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:12][CH2:11]2)O)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)(=O)C.S(=O)(=O)(O)O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)=[C:10]2[CH2:11][CH2:12][N:13]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14407073alpha,alpha-Bis(4-fluorophenyl)-1-(phenylsulfonyl)-4-piperidinemethanol

Product 1

HCID 144071694-[Bis(4-fluorophenyl)methylene]-1-(phenylsulfonyl)piperidine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 5.23 g (0.0118 mole) of α,α-bis(4-fluorophenyl)-1-(phenylsulfonyl)-4-piperidinemethanol in 100 ml of acetic acid and 20 ml of 2M sulfuric acid was heated at reflux for 2.5 hours and then poured over ice. The mixture was made basic with 50% sodium hydroxide and the basic mixture was extracted with methylene chloride. The methylene chloride solution was dried (anhydrous sodium sulfate), and the solvent was removed in vacuo. The residue was recrystallized from ether-hexane to give 3.23 g (64.4%) of white, crystalline, solid, m.p. 90°-92.5° C.

Workup

  1. temperatureat reflux for 2.5 hours
  2. additionpoured over ice
  3. extractionthe basic mixture was extracted with methylene chloride
  4. dry with materialThe methylene chloride solution was dried (anhydrous sodium sulfate)
  5. customthe solvent was removed in vacuo
  6. customThe residue was recrystallized from ether-hexane
  7. customto give 3.23 g (64.4%) of white, crystalline, solid, m.p. 90°-92.5° C.

Sources & evidence

ORD record
ord-be7a5c0e8bd44ceb98e02a208d41295b
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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