Diethyl Ether → N-[4-(1-hydroxy-1-methylethyl)phenyl]-3-(piperidin-1-ylsulfonyl)benzamide

HRID 1967510Notes

Reaction equation

HRID 1967510 reaction equation
C[Li].[CH2:3](OCC)C.[C:8]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:34])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([S:25]([N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)(=[O:27])=[O:26])[CH:20]=2)=[CH:13][CH:12]=1)(=[O:10])[CH3:9]>O>[OH:10][C:8]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:34])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([S:25]([N:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]3)(=[O:27])=[O:26])[CH:20]=2)=[CH:13][CH:12]=1)([CH3:3])[CH3:9]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 1127074N-(4-acetylphenyl)-3-(piperidin-1-ylsulfonyl)benzamideHCID 178418348HCID 178418348, compound

Product 1

HCID 66872323N-[4-(1-hydroxy-1-methylethyl)phenyl]-3-(piperidin-1-ylsulfonyl)benzamideYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

With cooling with ice, methyllithium (0.66 mL, 0.98 M diethyl ether solution) was dropwise added to a diethyl ether (1.0 mL) solution of the compound (50.0 mg) obtained in Example 92, and stirred for 1 hour with cooling with ice. After heated up to room temperature, water was added to the reaction liquid, and then extracted three times with ethyl acetate. This was dried with sodium sulfate, then the drying agent was removed through filtration, and the solvent was evaporated off under reduced pressure. The residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 80%, gradient) to give the entitled compound (51.1 mg, 99%) as a white solid.

Workup

  1. temperaturewith cooling with ice
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThis was dried with sodium sulfate
  4. customthe drying agent was removed through filtration
  5. customthe solvent was evaporated off under reduced pressure
  6. customThe residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 80%, gradient)

Sources & evidence

ORD record
ord-1724d573a73c404499a435eb85d25bae
Source dataset
uspto-grants-2013_04
Patent number
US08420823B2

Reaction notes

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