Water → HCID 18919735, compound

HRID 1291201Notes

Reaction equation

HRID 1291201 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([S:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I([O-])(=O)(=O)=[O:23].[Na+].O.[OH-].[Na+]>O.CO>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([S:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:23])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 18919778HCID 18919778, compoundHCID 23667635Sodium periodate

Product 1

HCID 18919735HCID 18919735, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

0.37 g (0.00124 mol) of 1-benzyl-4-benzylsulfanyl-piperidine was suspended in a mixture of 20 ml of water/methanol (1:1) and treated with 2.66 g (0.0124 mol) of sodium periodate. The mixture was stirred at room temperature for 3 hrs., 150 ml of water were added, the pH was adjusted to 8-9 with 1N aqueous NaOH, the mixture was extracted with ethyl acetate and the organic phase was dried over magnesium sulfate. The solvent was removed on a rotary evaporator and the residue was chromatographed on silica gel with methanol/dichloro-methane (1:19). The fraction having Rf 0.31 was the desired product. 0.17 g (44%) of (RS)-1-benzyl-4-benzylsulfinyl-piperidine was obtained as white crystals; m.p. 123°-125`0.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialthe organic phase was dried over magnesium sulfate
  3. customThe solvent was removed on a rotary evaporator
  4. customthe residue was chromatographed on silica gel with methanol/dichloro-methane (1:19)

Sources & evidence

ORD record
ord-e2c6a43bb63d4df7b960957c61ccad18
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

Loading…