Ethanol → HCID 70873479, compound

HRID 2172193Notes

Reaction equation

HRID 2172193 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)C.O1CCCCC1[O:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][CH:32]([O:35][CH2:36][C:37]3[O:38][C:39]4[CH:45]=[CH:44][C:43]([C:46]([F:49])([F:48])[F:47])=[CH:42][C:40]=4[CH:41]=3)[CH2:31][CH2:30]2)=[CH:25][CH:24]=1>O>[F:49][C:46]([F:47])([F:48])[C:43]1[CH:44]=[CH:45][C:39]2[O:38][C:37]([CH2:36][O:35][CH:32]3[CH2:33][CH2:34][N:29]([C:26]4[CH:27]=[CH:28][C:23]([OH:22])=[CH:24][CH:25]=4)[CH2:30][CH2:31]3)=[CH:41][C:40]=2[CH:42]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 70873461HCID 70873461, compound

Product 1

HCID 70873479HCID 70873479, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

p-Toluenesulfonic acid monohydrate (0.84 g) was added to an ethanol solution (40 ml) of 1-[4-(tetrahydropyran-2-yloxy)phenyl]-4-(5-trifluoromethylbenzofuran-2-ylmethoxy)piperidine (2.1 g) and the mixture was heated at reflux for 1 hour. After being cooled to room temperature, water was added to the reaction mixture and filtered through Celite, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over sodium sulfate, and then concentrated under reduced pressure. The residue was washed with ether and dried to afford the title compound as a white powder (1.4 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 hour
  3. filtrationfiltered through Celite
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washThe residue was washed with ether
  9. customdried

Sources & evidence

ORD record
ord-e9bbed7d71d84181b1c661b7702a3d8a
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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