Methanesulfonic Acid → {4-[(2-Pyridin-3-ylpiperidin-1-yl)sulfonyl]phenyl}amine

HRID 421554Notes

Reaction equation

HRID 421554 reaction equation
CS(O)(=O)=O.[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][N:13]2[S:18]([C:21]2[CH:26]=[CH:25][C:24]([NH:27]C(=O)C)=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH:7]=1.C(=O)(O)[O-].[Na+]>CO>[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][N:13]2[S:18]([C:21]2[CH:22]=[CH:23][C:24]([NH2:27])=[CH:25][CH:26]=2)(=[O:20])=[O:19])[CH:7]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 659759N-(4-{[2-(pyridin-3-yl)piperidin-1-yl]sulfonyl}phenyl)acetamide

Product 1

HCID 2770922{4-[(2-Pyridin-3-ylpiperidin-1-yl)sulfonyl]phenyl}amineYield 78.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1.81 ml portion of methanesulfonic acid was added to a methanol solution (10 ml) of 1.0 g N-(4-{[2-(pyridin-3-yl)piperidin-1-yl]sulfonyl}phenyl)acetamide and stirred overnight at room temperature. The reaction liquid was poured into ice water and neutralized with sodium bicarbonate, and then layer separation operation was carried out by adding ethyl acetate. The organic layer was washed with saturated sodium chloride aqueous solution, dried with anhydrous sodium sulfate and then concentrated under a reduced pressure to obtain 695 mg of 4-{[2-(pyridin-3-yl)piperidin-1-yl]sulfonyl}aniline as pale yellow crystals.

Workup

  1. customThe reaction liquid
  2. customlayer separation operation
  3. additionby adding ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride aqueous solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-4b59a8b4d78b455c86b6d0f266d83bd8
Source dataset
uspto-grants-2012_01
Patent number
US08101580B2

Reaction notes

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