Benzyl mercaptan → HCID 18919778, compound

HRID 1291200Notes

Reaction equation

HRID 1291200 reaction equation
[H-].[Na+].[CH2:3]([SH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CS(O[CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][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>[CH2:22]([N:19]1[CH2:20][CH2:21][CH:16]([S:10][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:17][CH2:18]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 7509Benzyl mercaptanHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 4362638HCID 4362638, compound

Product 1

HCID 18919778HCID 18919778, compoundYield 40.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

0.8 g (0.02 mol) of sodium hydride (60% dispersion in oil) was washed three times with hexane and suspended in 20 ml of THF. 2.24 ml (0.019 mol) of benzyl mercaptan in 12 ml of THF were added dropwise at 0°. The mixture was stirred at room temperature for 15 min. and subsequently 0.95 g (0.0037 mol) of 1-benzylpiperidin-4-yl methanesulfonate in 10 ml of THF was added dropwise. The reaction mixture was boiled at reflux for 22 hrs. and then poured into 200 ml of 2N aqueous NaOH. The inorganic phase was extracted with ether and the combined organic phases were washed with 2N aqueous NaOH and dried over magnesium sulfate. The residue was chromatographed on silica gel with ethyl acetate/hexane (1:3→1:1) as the eluent. 0.444 g (40%) of 1-benzyl-4-benzylsulfanylpiperidine was obtained as a yellow oil. MS: me/e (% basic peak)=297 (C19H23 NS+, 1.4), 206 (62), 174 (23), 91 (199).

Workup

  1. temperatureat reflux for 22 hrs
  2. extractionThe inorganic phase was extracted with ether
  3. washthe combined organic phases were washed with 2N aqueous NaOH
  4. dry with materialdried over magnesium sulfate
  5. customThe residue was chromatographed on silica gel with ethyl acetate/hexane (1:3→1:1) as the eluent

Sources & evidence

ORD record
ord-3deea9a1032d4dfd84ef909860262e5e
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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