Phenol → 4-(4-Chlorobenzene-1-sulfonyl)piperidine--hydrogen chloride (1/1)

HRID 1981793Notes

Reaction equation

HRID 1981793 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]2[CH2:16][CH2:15][N:14](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C1(O)C=CC=CC=1>Br>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 996PhenolHCID 13607949HCID 13607949, compound

Product 1

HCID 27610714-(4-Chlorobenzene-1-sulfonyl)piperidine--hydrogen chloride (1/1)Yield 104.3%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture of 10.14 g (0.0246 mole) of 4-[(4-chlorophenyl)sulfonyl]-1-[(4-methylphenyl)sulfonyl]piperidine and 40 ml of phenol in 120 ml of 48% hydrobromic acid was refluxed for one hr and quenched in 800 ml of water. The mixture was made basic with 50% sodium hydroxide and then extracted with methylene chloride. The methylene chloride extract was dried over magnesium sulfate and the volume was reduced to 200 ml in vacuo. Excess ethereal hydrogen chloride was added to give a white precipitate, the hydrochloride salt. Recrystallization of the salt from methanol-diethyl ether gave 3.80 g (52.0%) of a crystalline solid, m.p. 280°-281.5° C. with decomposition. An additional 0.77 g (10.6%) of product was obtained from the filtrate.

Workup

  1. temperaturewas refluxed for one hr
  2. customquenched in 800 ml of water
  3. extractionextracted with methylene chloride
  4. extractionThe methylene chloride extract
  5. dry with materialwas dried over magnesium sulfate
  6. additionExcess ethereal hydrogen chloride was added
  7. customto give a white precipitate
  8. customRecrystallization of the salt from methanol-diethyl ether

Sources & evidence

ORD record
ord-e552dba7e19a404899f9cc23386282d3
Source dataset
uspto-grants-1986_06
Patent number
US04593102

Reaction notes

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