p-Toluenesulfonic acid → HCID 13607955, compound

HRID 1981780Notes

Reaction equation

HRID 1981780 reaction equation
C(=O)(O)[O-].[Na+].[C:6]1([SH:12])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([OH:23])(=[O:22])=O)=[CH:16][CH:15]=1.[OH-].[Na+].O[CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][NH:30][CH2:29]1>CN(C)C=O>[CH3:13][C:14]1[CH:15]=[CH:16][C:17]([S:20]([N:30]2[CH2:31][CH2:32][CH2:33][CH:28]([CH2:27][S:12][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:29]2)(=[O:22])=[O:23])=[CH:18][CH:19]=1

Participants

7

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 107308Piperidin-3-ylmethanolHCID 516892Sodium Bicarbonate

Product 1

HCID 13607955HCID 13607955, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

To a mixture of 130 g (1.23 mole) of sodium bicarbonate and 145 g (1.32 mole) of thiophenol in 1.5 liters of dimethylformamide (which had stirred at room temperature for about 1 hr) was added 1-[(4-methylphenyl)sulfonyl]-3-piperidinemethanol ester with 4-methylbenzenesulfonic acid (the oil produced in Preparation 23) in 500 ml of dimethylformamide. The mixture was stirred at 80° C. for 12 hours and then at room temperature for 48 hr. One liter of dilute sodium hydroxide was added and the mixture was stirred for 2 hr. A viscous gum formed. The gum was separated and dissolved in methylene chloride. The resulting solution was extracted with several portions of dilute aqueous sodium hydroxide. The methylene chloride phase was dried over magnesium sulfate and the solvent was removed in vacuo. The residue was recrystallized from diethyl ether-methylene chloride to give 221.4 g (72% based on starting 3-(hydroxymethyl)piperidine in Preparation 23) of white crystalline solid, m.p. 72°-75° C.

Workup

  1. waitat room temperature for 48 hr
  2. stirringthe mixture was stirred for 2 hr
  3. customA viscous gum formed
  4. customThe gum was separated
  5. dissolutiondissolved in methylene chloride
  6. extractionThe resulting solution was extracted with several portions of dilute aqueous sodium hydroxide
  7. dry with materialThe methylene chloride phase was dried over magnesium sulfate
  8. customthe solvent was removed in vacuo
  9. customThe residue was recrystallized from diethyl ether-methylene chloride
  10. customto give

Sources & evidence

ORD record
ord-15a3b287be454c0db48d52a25f978a74
Source dataset
uspto-grants-1986_06
Patent number
US04593102

Reaction notes

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