4-Methoxybenzenesulfonyl chloride → HCID 51001227, compound

HRID 2381175Notes

Reaction equation

HRID 2381175 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2([F:19])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:12])=[CH:6][CH:5]=1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>N1C=CC=CC=1>[F:21][C:2]([F:20])([F:1])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2([F:19])[CH2:18][CH2:17][N:16]([S:30]([C:27]3[CH:26]=[CH:25][C:24]([O:23][CH3:22])=[CH:29][CH:28]=3)(=[O:32])=[O:31])[CH2:15][CH2:14]2)=[O:12])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 86652004HCID 86652004, compound

Product 1

HCID 51001227HCID 51001227, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Fluoro-piperidine-4-carboxylic acid (4-trifluoromethoxy-phenyl)-amide (0.1 g) and 4-methoxybenzenesulfonyl chloride (0.067 g) were dissolved in pyridine (10 ml) at RT and under an argon atmosphere and stirred for 24 h at RT. The solvent was evaporated off, the residue was absorbed on silica gel and purified by flash chromatography (AcOEt/heptane, gradient from 0 to 25%) to give the desired 4-fluoro-1-(4-methoxy-benzenesulfonyl)-piperidine-4-carboxylic acid (4-trifluoromethoxy-phenyl)-amide (0.075 g) as a white solid. MS (ESI): 475.1 (MH+).

Workup

  1. customThe solvent was evaporated off
  2. customthe residue was absorbed on silica gel
  3. custompurified by flash chromatography (AcOEt/heptane, gradient from 0 to 25%)

Sources & evidence

ORD record
ord-1185b2bfa74e4351b18cf1a2a676410d
Source dataset
uspto-grants-2012_09
Patent number
US08258158B2

Reaction notes

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