Potassium Hydroxide → N-Cyclopropyl-N-{1-[2-(2-hydroxy-ethylamino)-benzoyl]-piperidin-4-yl}-3-trifluoromethyl-benzenesulfonamide

HRID 1428963Notes

Reaction equation

HRID 1428963 reaction equation
[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][N:21]([C:24](=[O:37])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[N:31]3[CH2:35][CH2:34][O:33]C3=O)[CH2:20][CH2:19]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.[OH-].[K+]>O>[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][N:21]([C:24](=[O:37])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[NH:31][CH2:35][CH2:34][OH:33])[CH2:20][CH2:19]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:16])([F:17])[F:15])[CH:9]=2)(=[O:6])=[O:7])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 58002115N-Cyclopropyl-N-{1-[2-(2-oxo-oxazolidin-3-yl)-benzoyl]-piperidin-4-yl}-3-trifluoromethyl-benzenesulfonamide

Product 1

HCID 24860817N-Cyclopropyl-N-{1-[2-(2-hydroxy-ethylamino)-benzoyl]-piperidin-4-yl}-3-trifluoromethyl-benzenesulfonamideYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

N-Cyclopropyl-N-{1-[2-(2-oxo-oxazolidin-3-yl)-benzoyl]-piperidin-4-yl}-3-trifluoromethyl-benzenesulfonamide (12) (0.110 g, 0.20 mmol) was taken up in 3 ml of ETOH and 0.5 ml of water. To the mixture, KOH (0.046 g, 0.82 mmol) was added. The mixture was heated at 100° C. and stirred for 2 hours. The reaction mixture was concentrated to dryness under reduced pressure. Then residue was dissolved in EtOAc (30 ml) and the mixture was washed with H2O (15 ml) and brine (15 ml). The organic layer was dried over MgSO4 and concentrated to dryness. The crude product was purified through a column of silica gel with a gradient of 90% to 100% EtOAc in hexane to afford the title compound 13 (pale yellow solid, 81 mg, 83%). LC: 100%. MS: m/z=511.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  2. dissolutionThen residue was dissolved in EtOAc (30 ml)
  3. washthe mixture was washed with H2O (15 ml) and brine (15 ml)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated to dryness
  6. customThe crude product was purified through a column of silica gel with a gradient of 90% to 100% EtOAc in hexane

Sources & evidence

ORD record
ord-a96b1cbe0b074b81b1e83b06b87ea2e3
Source dataset
uspto-grants-2015_01
Patent number
US08937181B2

Reaction notes

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