Phenol → HCID 70445962, compound

HRID 236104Notes

Reaction equation

HRID 236104 reaction equation
C1(O)C=CC=CC=1.[OH-].[Na+].[C:10]1([S:16][CH:17]2[CH2:22][CH2:21][CH2:20][NH:19][CH2:18]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]\[C:26]([OH:28])=[O:27]>Br>[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]\[C:26]([OH:28])=[O:27].[C:10]1([S:16][CH:17]2[CH2:22][CH2:21][CH2:20][NH:19][CH2:18]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 14798Sodium HydroxideHCID 444266Maleic AcidHCID 13608004HCID 13608004, compound

Product 1

HCID 70445962HCID 70445962, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

The above mixture was suspended in 600 ml of 48% hydrobromic acid and excess phenol. The suspension was refluxed for 1 hr and was cooled to room temperature. The reaction mixture was made basic with 50% aqueous sodium hydroxide and the basic solution was extracted with methylene chloride. The methylene chloride extract was extracted with 2M sulfuric acid. The acidic aqueous phase was made basic with 50% sodium hydroxide and the basic solution was extracted with methylene chloride. This last methylene chloride solution was dried over magnesium sulfate and the solvent was removed in vacuo to give the free base: 3-(phenylthio)piperidine as an oil. The free base was reacted with maleic acid and the maleate salt was recrystallized from methanol-diethyl ether as white crystals, m.p. 117°-119° C.

Workup

  1. temperatureThe suspension was refluxed for 1 hr
  2. extractionthe basic solution was extracted with methylene chloride
  3. extractionThe methylene chloride extract
  4. extractionwas extracted with 2M sulfuric acid
  5. extractionthe basic solution was extracted with methylene chloride
  6. dry with materialThis last methylene chloride solution was dried over magnesium sulfate
  7. customthe solvent was removed in vacuo
  8. customto give the free base
  9. customthe maleate salt was recrystallized from methanol-diethyl ether as white crystals, m.p. 117°-119° C.

Sources & evidence

ORD record
ord-41df64cc6bda413f93360958b16cdf68
Source dataset
uspto-grants-1987_02
Patent number
US04642348

Reaction notes

Loading…