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

HRID 1460237Notes

Reaction equation

HRID 1460237 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)piperidineYield 64.4%

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, mp 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

Sources & evidence

ORD record
ord-38bbb56026f14c8caad4082fb3bcbeab
Source dataset
uspto-grants-1991_12
Patent number
US05070087

Reaction notes

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