Sodium Chloride → 4-(4-Methoxybenzylthio)-1-methylpiperidine

HRID 5092

반응식

HRID 5092 반응식
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][SH:8])=[CH:5][CH:4]=1.[H-].[Na+].CS(O[CH:18]1[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]1)(=O)=O.[Cl-].[Na+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][S:8][CH:18]2[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]2)=[CH:5][CH:4]=1

참가 물질

6

반응물 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 804074-Methoxy-alpha-toluenethiolHCID 41906811-Methylpiperidin-4-yl methanesulfonate

생성물 1

HCID 197972594-(4-Methoxybenzylthio)-1-methylpiperidine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

10.9 ml of 4-methoxybenzyl mercaptan were dissolved in 55 ml of dry dimethylformamide, and 3.4 g of sodium hydride (as a 55% w/w suspension in mineral oil) were added to the solution, whilst ice-cooling. The mixture was then stirred at room temperature for 30 minutes. At the end of this time, a solution of 12.6 g of 4-methanesulfonyloxy-1-methylpiperidine in 63 ml of dry dimethylformamide was added to the mixture, which was then allowed to stand overnight at room temperature. The reaction mixture was then poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract as washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel (eluted with a 1:4 by volume mixture of ethyl acetate and methanol) to afford 9.01 g of the title compound as an oil.

후처리

  1. temperaturecooling
  2. waitto stand overnight at room temperature
  3. extractionextracted with ethyl acetate
  4. extractionThe extract
  5. washas washed with an aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was then removed by distillation under reduced pressure
  8. customthe residue was purified by column chromatography through silica gel (
  9. washeluted with a 1:4 by volume mixture of ethyl acetate and methanol)

출처 및 근거

ORD 기록
ord-f4333880ec444bb9b8b94a7c224f7aa8
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05242914

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