Thiophenol → Phenyl{4-[(phenylsulfanyl)methyl]piperidin-1-yl}methanone

HRID 1291197Notes

Reaction equation

HRID 1291197 reaction equation
[H-].[Na+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CS(O[CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:18][CH2:17]1)(=O)=O.[OH-].[Na+]>CCCCCC.C1COCC1>[C:22]([N:19]1[CH2:20][CH2:21][CH:16]([CH2:15][S:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:17][CH2:18]1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 99947861-Benzoylpiperidin-4-ylmethyl methanesulfonate

Product 1

HCID 67623230Phenyl{4-[(phenylsulfanyl)methyl]piperidin-1-yl}methanoneYield 93.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

4.27 g (0.1068 mol) of sodium hydride (60% dispersion in oil) were washed twice with hexane, suspended in 160 ml of THF and treated with 10.3 ml (0.1068 mol) of thiophenol. The mixture was stirred for 15 min. and then a solution of 5.95 g (0.02 mol) of 1-benzoylpiperidin-4-yl-methyl methanesulfonate in 20 ml of THF was added. The mixture was boiled at reflux for 18 hrs. The reaction mixture was treated with 250 ml of 2N aqueous NaOH and extracted with ether. The organic phase was washed with 2N aqueous NaOH and saturated sodium chloride solution, dried over sodium sulfate and concentrated. The residue was chromatographed on silica gel with ethyl acetate/hexane (1:3) as the eluent. 5.8 g (93%) of 1-benzoyl-4thio-phenoxymethylpiperidine were obtained as yellow crystals; m.p. 76°-79°.

Workup

  1. temperatureat reflux for 18 hrs
  2. extractionextracted with ether
  3. washThe organic phase was washed with 2N aqueous NaOH and saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel with ethyl acetate/hexane (1:3) as the eluent

Sources & evidence

ORD record
ord-f307bf6aac1d419b9f5b98cee6c7b92d
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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