Hydrogen Bromide → HCID 20217956, compound

HRID 236103Notes

Reaction equation

HRID 236103 reaction equation
ClC1C=CC=CC=1S.C(=O)([O-])[O-].[Na+].[Na+].S([N:25]1[CH2:30][CH2:29][CH2:28][CH:27]([S:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[Cl:38])[CH2:26]1)(C1C=CC(C)=CC=1)(=O)=O.C1(O)C=CC=CC=1.[BrH:46]>CN(C)C=O>[BrH:46].[Cl:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[S:31][CH:27]1[CH2:28][CH2:29][CH2:30][NH:25][CH2:26]1

Participants

7

Reactant 5

HCID 260Hydrogen BromideHCID 996PhenolHCID 10340Sodium CarbonateHCID 80599o-ChlorothiophenolHCID 70445932HCID 70445932, compound

Product 1

HCID 20217956HCID 20217956, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 51.13 g (0.125 mole) of 3-phenylsulfonic acid ester with 1-[(4-methylbenzene)sulfonyl)-3-piperidinol, 25.2 g (0.175 mole) of o-chlorothiophenol and 58 g of sodium carbonate in dimethylformamide was heated at 100° C. for 19 hr and then was quenched in 1 liter of dilute sodium hydroxide. The mixture was extracted with several portions of methylene chloride. The combined methylene chloride extract was washed with several portions of 1M sodium hydroxide, dried over magnesium sulfate and evaporated in vacuo to give an oil which was shown by NMR and mass spectroscopy to be N-tosyl-3-(o-chlorothiophenoxy)piperidine. A mixture of the oil and excess phenol in 200 ml of 48% hydrobromic acid was refluxed for 1.5 hr. The reaction mixture was quenched in ice water, made basic with sodium hydroxide and extracted with several portions of methylene chloride. The combined methylene chloride extract was dried over magnesium sulfate and evaporated in vacuo to give an oil, the free base of the title compound. The free base was converted to the hydrobromic acid salt which was recrystallized from isopropanol-acetonitrile-isopropyl ether, m.p. 152.5°-154.5° C.

Workup

  1. customwas quenched in 1 liter of dilute sodium hydroxide
  2. extractionThe mixture was extracted with several portions of methylene chloride
  3. extractionThe combined methylene chloride extract
  4. washwas washed with several portions of 1M sodium hydroxide
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customto give an oil which
  8. temperaturewas refluxed for 1.5 hr
  9. customThe reaction mixture was quenched in ice water
  10. extractionextracted with several portions of methylene chloride
  11. extractionThe combined methylene chloride extract
  12. dry with materialwas dried over magnesium sulfate
  13. customevaporated in vacuo
  14. customto give an oil

Sources & evidence

ORD record
ord-e483341d2f2b4e9e9ee294905738e732
Source dataset
uspto-grants-1987_02
Patent number
US04642348

Reaction notes

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