Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 67275611, compound

HRID 2172185Notes

Reaction equation

HRID 2172185 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O1CCCCC1[O:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]2[CH2:36][CH2:35][CH:34]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][C:46]([F:49])([F:48])[F:47])=[CH:41][CH:40]=3)[CH2:33][CH2:32]2)=[CH:27][CH:26]=1>C(O)C>[F:48][C:46]([F:47])([F:49])[O:45][C:42]1[CH:41]=[CH:40][C:39]([CH2:38][O:37][CH:34]2[CH2:35][CH2:36][N:31]([C:28]3[CH:29]=[CH:30][C:25]([OH:24])=[CH:26][CH:27]=3)[CH2:32][CH2:33]2)=[CH:44][CH:43]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 70873872HCID 70873872, compound

Product 1

HCID 67275611HCID 67275611, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

Pyridinium p-toluenesulfonate (81 mg) was added to an ethanol solution (3 ml) of 1-[4-(tetrahydropyran-2-yloxy)phenyl]-4-(4-trifluoromethoxybenzyloxy)piperidine (507 mg) and the mixture was stirred at 70 to 80° C. for 24 hours. After being cooled to room temperature, the reaction mixture was concentrated under reduced pressure, ethyl acetate and a saturated sodium hydrogen carbonate aqueous solution were added to the residue, and the result was separated into layers. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over magnesium sulfate. After being concentrated under reduced pressure, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to afford the title compound as a pale purple solid (305 mg).

Workup

  1. temperatureAfter being cooled to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure, ethyl acetate
  3. additiona saturated sodium hydrogen carbonate aqueous solution were added to the residue
  4. customthe result was separated into layers
  5. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationAfter being concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-a9878beff5584fe387fa49e7290ba246
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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