Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → SS-3227

HRID 856104Notes

Reaction equation

HRID 856104 reaction equation
O1CCCCC1[O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][CH:17]([O:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=3)[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[F:31][C:28]([F:29])([F:30])[O:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][CH:17]2[CH2:16][CH2:15][N:14]([C:11]3[CH:12]=[CH:13][C:8]([OH:7])=[CH:9][CH:10]=3)[CH2:19][CH2:18]2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 160991421-[4-(Tetrahydropyran-2-yloxy)phenyl]-4-(4-trifluoromethoxyphenoxy)piperidine

Product 1

HCID 11653258SS-3227Yield 94.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-[4-(tetrahydropyran-2-yloxy)phenyl]-4-(4-trifluoromethoxyphenoxy)piperidine (30.1 g, 68.8 mmol) prepared in Reference Example 191 and pyridinium p-toluene sulfonate (5.2 g, 20.6 mmol) in ethanol (450 ml) was stirred at 70° C. for 24 hours. The reaction mixture was concentrated under reduced pressure, and methylene chloride and a saturated sodium hydrogencarbonate aqueous solution were added to the residue, which was stirred for a while. The mixture was extracted with methylene chloride, and the extract was dried over magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=10/1) to afford 4-[4-(4-trifluoromethoxyphenoxy)-piperidin-1-yl]phenol (22.9 g, yield 94%) as a a pale brown powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and methylene chloride
  2. additiona saturated sodium hydrogencarbonate aqueous solution were added to the residue, which
  3. stirringwas stirred for a while
  4. extractionThe mixture was extracted with methylene chloride
  5. dry with materialthe extract was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-bc32df09b30e4a4c97a7a97e01e4030a
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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