Hydrochloric Acid → HCID 15451769, compound

HRID 399938Notes

Reaction equation

HRID 399938 reaction equation
[Cl:1][C:2]1[C:10]([N:11]2[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]2)=[C:9]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[H-].[Na+].[CH3:24]I.Cl>O1CCCC1.O>[Cl:1][C:2]1[C:10]([N:11]2[CH2:12][CH2:13][CH:14]([O:17][CH3:24])[CH2:15][CH2:16]2)=[C:9]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15451768HCID 15451768, compound

Product 1

HCID 15451769HCID 15451769, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Chloro-3-(4-hydroxypiperidin-1-yl)-4-methylsulfonylbenzoic acid (0.70 g, 2.1 mmol) was added with stirring to a suspension of 0.25 g (6.3 mmol) of sodium hydride in a mixture of 0.40 mL (6.4 mmol) of methyl iodide and 10 mL of dry tetrahydrofuran. The mixture was heated to reflux and stirred for 24 hr. The resulting mixture was treated with water, acidified with 1N aqueous hydrochloric acid and extracted several times with dichloromethane. The organic layers were combined and dried over magnesium sulfate, the solvent was removed by concentration under reduced pressure, and the residue was rinsed with petroleum ether to obtain 0.70 g (96 percent of theory) of the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. extractionextracted several times with dichloromethane
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was removed by concentration under reduced pressure
  6. washthe residue was rinsed with petroleum ether

Sources & evidence

ORD record
ord-f2b5f25b9a52437c9255526edf24f3b4
Source dataset
uspto-grants-1998_10
Patent number
US05824802

Reaction notes

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