Phenol → 4-(2-Chlorophenylsulfanyl)piperidine hydrochloride

HRID 236101

Reaction equation

HRID 236101 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH:9]1[CH2:14][CH2:13][N:12](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:11][CH2:10]1.C1(O)C=CC=CC=1.[OH-].[Na+]>Br>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 996PhenolHCID 14798Sodium HydroxideHCID 136079634-[(2-Chlorophenyl)thio]-1-[(4-methylphenyl)sulfonyl]piperidine

Product 1

HCID 177498024-(2-Chlorophenylsulfanyl)piperidine hydrochloride

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture of 88.76 g (0.23 mole) of 4-[(2-chlorophenyl)thio]-1-[(4-methylphenyl)sulfonyl]piperidine, 47.0 g (0.50 mole) of phenol and 200 ml of 48% hydrobromic acid was refluxed for 1.5 hr. The reaction mixture was cooled to room temperature and diluted with ice water. The mixture was made alkaline with 50% sodium hydroxide and extracted with diethyl ether. The ether phase was extracted with 1N sulfuric acid. The acidic layer was made alkaline and extracted with methylene chloride. The methylene chloride layer was dried over sodium sulfate, filtered and evaporated to give an oil, the free base of the title compound. The free base was converted to 4.30 g (36.5%) of a white crystalline hydrochloride salt, m.p. 202°-210° C.

Workup

  1. temperaturewas refluxed for 1.5 hr
  2. extractionextracted with diethyl ether
  3. extractionThe ether phase was extracted with 1N sulfuric acid
  4. extractionextracted with methylene chloride
  5. dry with materialThe methylene chloride layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto give an oil

Sources & evidence

ORD record
ord-2fd37515aeae47f5b6dce823bd9360b4
Source dataset
uspto-grants-1987_02
Patent number
US04642348

Linked notes

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