Thiophenol → 3-Hydroxy-1-methyl-4-phenyl-4-phenylthio-piperidine

HRID 895046Notes

Reaction equation

HRID 895046 reaction equation
[OH-].[Na+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O:10]1[C:16]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]1[CH2:12][N:13]([CH3:23])[CH2:14][CH2:15]2>C(O)CO>[OH:10][CH:11]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([S:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:15][CH2:14][N:13]([CH3:23])[CH2:12]1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 4350913-Methyl-6-phenyl-7-oxa-3-azabicyclo[4.1.0]heptane

Product 1

HCID 129293683-Hydroxy-1-methyl-4-phenyl-4-phenylthio-piperidineYield 86.8%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

9.6 Ml of 10% sodium hydroxide solution was added to a solution of 2.46 ml (0.024 mole) of thiophenol in 15 ml of ethylene glycol and the resulting solution stirred at room temperature for five minutes. 1.9 G (0.01 mole) of 3,4-epoxy-1-methyl-4-phenyl-piperidine was added with stirring to the above solution and the resulting solution stirred at room temperature for a further one hour. A solid began to separate after five minutes. The solid was filtered and suspended in acetone. Filtration of the solid gave 2.6 g of 3-hydroxy-1-methyl-4-phenyl-4-phenylthio-piperidine as a white solid having a melting point of 217°-9° C.

Workup

  1. stirringwith stirring to the above solution
  2. stirringthe resulting solution stirred at room temperature for a further one hour
  3. customto separate after five minutes
  4. filtrationThe solid was filtered
  5. filtrationFiltration of the solid

Sources & evidence

ORD record
ord-78db829290b64018a583c854a0d0133c
Source dataset
uspto-grants-1981_08
Patent number
US04286095

Reaction notes

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