Pyridine → 4-(4-Methoxyphenyl)-1-(toluene-4-sulfonyl)piperidine

HRID 655649Notes

Reaction equation

HRID 655649 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.N1C=CC=CC=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1>O>[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([CH:26]2[CH2:31][CH2:30][N:29]([S:7]([C:4]3[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=3)(=[O:9])=[O:8])[CH2:28][CH2:27]2)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 106792704-(4-Methoxyphenyl)piperidine

Product 1

HCID 574825524-(4-Methoxyphenyl)-1-(toluene-4-sulfonyl)piperidineYield 66.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

p-Toluenesulfonyl chloride (4.39 g, 23 mmol) was added to a pyridine solution (30 ml) of 4-(4-methoxyphenyl)piperidine (4.0 g, 21 mmol) and the mixture was stirred at room temperature overnight. Water was added to the solution mixture, which was then extracted with ethyl acetate. The organic phase was washed with hydrochloric acid and water, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1). The purified product was concentrated to dryness under reduced pressure to obtain 4-(4-methoxyphenyl)-1-(toluene-4-sulfonyl)piperidine (4.8 g) as white powder.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic phase was washed with hydrochloric acid and water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)
  6. concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-9798361a65484e0e9ff34a974969272c
Source dataset
uspto-grants-2011_12
Patent number
US08071600B2

Reaction notes

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