Potassium Hydroxide → 4-(2-Methylsulfonyl-4-methoxyphenyl)piperidine

HRID 840418Notes

Reaction equation

HRID 840418 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:16][CH2:15][N:14](C(OCC3C=CC=CC=3)=O)[CH2:13][CH2:12]2)=[C:7]([S:27]([CH3:30])(=[O:29])=[O:28])[CH:6]=1>CCO>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[C:7]([S:27]([CH3:30])(=[O:29])=[O:28])[CH:6]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 226222304-(4-Methoxy-2-methylsulfonylphenyl)-n-cbz-piperidine

Product 1

HCID 226223344-(2-Methylsulfonyl-4-methoxyphenyl)piperidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of KOH (1.50 g) in 20 mL of 1:1 EtOH:H20 was added 1.23 g of 4-(4-methoxy-2-methylsulfonylphenyl)-N-Cbz-piperidine. The resulting mixture was heated reflux under N2 atmosphere for 18 h, evaporated, dissolved in 10 mL H2O, and extracted with CHCl3. The organic extracts were combined, dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting residue was purified by chromatography (20:1 DCM in methanol containing 0.5% aqueous NH4OH). MS m/z 270 (M+H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperaturereflux under N2 atmosphere for 18 h
  3. customevaporated
  4. dissolutiondissolved in 10 mL H2O
  5. extractionextracted with CHCl3
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by chromatography (20:1 DCM in methanol containing 0.5% aqueous NH4OH)

Sources & evidence

ORD record
ord-e045776662a64bcb976e49b4b19ce233
Source dataset
uspto-grants-2002_04
Patent number
US06365602B1

Reaction notes

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