p-Toluenesulfonic acid → HCID 20217759, compound

HRID 1981781Notes

Reaction equation

HRID 1981781 reaction equation
O[CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][NH:4]1.[S:9](Cl)([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10].CC1C=CC(S(O)(=O)=O)=CC=1.[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([SH:38])=[CH:34][CH:33]=1.C(=O)([O-])[O-].[Na+].[Na+]>N1C=CC=CC=1.CN(C)C=O>[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([S:38][CH2:2][CH:3]2[CH2:8][CH2:7][CH2:6][CH2:5][N:4]2[S:9]([C:12]2[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:34][CH:33]=1

Participants

8

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 73974-Toluenesulfonyl chlorideHCID 7815p-ChlorothiophenolHCID 10340Sodium CarbonateHCID 94263Piperidin-2-ylmethanol

Product 1

HCID 20217759HCID 20217759, compoundYield 43.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 57.92 g (0.504 mole) of 2-hydroxymethylpiperidine and 236 g (1.24 mole) of tosylchloride in one liter of pyridine was stirred at 25° C. overnight. The mixture was quenched in water and the aqueous mixture was extracted with several portions of methylene chloride. The combined methylene chloride extract was extracted with 1M sulfuric acid solution followed by 1M aqueous sodium hydroxide, dried over magnesium sulfate and evaporated to give an oil which was shown by NMR and mass spectrometry to be 1-[(4-methylphenyl)sulfonyl]-2-piperidinemethanol ester with 4-methylbenzene sulfonic acid. A mixture of 40.78 g (0.0964 mole) of the oil, 24.60 g (0.171 mole) of p-chlorothiophenol and 25.4 g of sodium carbonate in 200 ml of dimethylformamide was stirred at 100° C. overnight and then quenched in dilute sodium hydroxide. The mixture was extracted with several portions of methylene chloride. The combined extract was extracted with several portions of 1M sodium hydroxide, dried over magnesium sulfate and evaporated in vacuo to give an oil. The oil was crystallized from ether-hexane to give 29.73 g of the solid product. On standing at room temperature, the solid melted.

Workup

  1. customThe mixture was quenched in water
  2. extractionthe aqueous mixture was extracted with several portions of methylene chloride
  3. extractionThe combined methylene chloride extract
  4. extractionwas extracted with 1M sulfuric acid solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customto give an oil which
  8. customquenched in dilute sodium hydroxide
  9. extractionThe mixture was extracted with several portions of methylene chloride
  10. extractionThe combined extract
  11. extractionwas extracted with several portions of 1M sodium hydroxide
  12. dry with materialdried over magnesium sulfate
  13. customevaporated in vacuo
  14. customto give an oil
  15. customThe oil was crystallized from ether-hexane

Sources & evidence

ORD record
ord-81a38878c93a4bedbac4e169a67c02d4
Source dataset
uspto-grants-1986_06
Patent number
US04593102

Reaction notes

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