Hydrogen Bromide → HCID 20217855, compound

HRID 1981791Notes

Reaction equation

HRID 1981791 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]2[CH2:16][CH2:15][CH2:14][N:13](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br.[C:28]1([OH:34])C=CC=C[CH:29]=1.[OH-:35].[Na+].CC[O:39][CH2:40][CH3:41]>>[C:40]([OH:39])(=[O:9])/[CH:41]=[CH:29]/[C:28]([OH:34])=[O:35].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]2[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 260Hydrogen BromideHCID 996PhenolHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 13607950HCID 13607950, compound

Product 1

HCID 20217855HCID 20217855, compound

Procedure

A mixture of 24.18 g (0.06 mole) of 3-[(4-chlorophenyl)sulfonyl]-1-[(4-methylphenyl)sulfonyl]piperidine, 200 ml of 48% hydrobromic acid and 200 g (2.0 moles) of phenol was refluxed for 1.5 hr. The reaction mixture was cooled and poured into ice. The mixture was carefully made alkaline with 50% sodium hydroxide solution and extracted with diethyl ether. The ether layer was separated and held. The water layer was extracted with methylene chloride and separated, discarding the aqueous phase. The methylene chloride extract was evaporated on a rotary evaporator to give an oil which was combined with the ether layer. The new ether solution was back-extracted with 10% sodium hydroxide solution and the water layer discarded. The ether layer was next extracted with 1N sulfuric acid and the ether layer discarded. The acidic aqueous phase was made alkaline and extracted with methylene chloride. The methylene chloride layer was separated, dried and filtered, and the solvent was removed in vacuo to give a light yellow oil, the free base of the title compound. The free base was dissolved in methanol and an equimolar amount of fumaric acid in methanol was added. Addition of diethyl ether gave crystalline fumarate salt. The yield of white salt after drying over night at 100° C. in vacuo was 11.18 g (49.6%), m.p. 186°-187° C.

Workup

  1. temperaturewas refluxed for 1.5 hr
  2. temperatureThe reaction mixture was cooled
  3. additionpoured into ice
  4. extractionextracted with diethyl ether
  5. customThe ether layer was separated
  6. extractionThe water layer was extracted with methylene chloride
  7. customseparated
  8. extractionThe methylene chloride extract
  9. customwas evaporated on a rotary evaporator
  10. customto give an oil which
  11. extractionThe new ether solution was back-extracted with 10% sodium hydroxide solution
  12. extractionThe ether layer was next extracted with 1N sulfuric acid
  13. extractionextracted with methylene chloride
  14. customThe methylene chloride layer was separated
  15. customdried
  16. filtrationfiltered
  17. customthe solvent was removed in vacuo
  18. customto give a light yellow oil

Sources & evidence

ORD record
ord-426a0519f5ee4c17982673429d313d3e
Source dataset
uspto-grants-1986_06
Patent number
US04593102

Reaction notes

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