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

HRID 1907373Notes

Reaction equation

HRID 1907373 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-9463e5b98b5f4957bfd55e2fefdaaee0
Source dataset
uspto-grants-2013_12
Patent number
US08598162B2

Reaction notes

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