Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 4-[4-(4-Trifluoromethoxyphenyl)piperazin-1-yl]phenol

HRID 856100Notes

Reaction equation

HRID 856100 reaction equation
O1CCCCC1[O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=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:30][C:27]([F:28])([F:29])[O:26][C:23]1[CH:24]=[CH:25][C:20]([N:17]2[CH2:18][CH2:19][N:14]([C:11]3[CH:12]=[CH:13][C:8]([OH:7])=[CH:9][CH:10]=3)[CH2:15][CH2:16]2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 23081199HCID 23081199, compound

Product 1

HCID 694797194-[4-(4-Trifluoromethoxyphenyl)piperazin-1-yl]phenolYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-[4-(tetrahydropyran-2-yloxy)phenyl]-4-(4-trifluoromethoxyphenyl)piperazine (2.65 g, 6.27 mmol) prepared in Reference Example 185 and pyridinium p-toluene sulfonate (473 mg, 1.88 mmol) in ethanol (50 ml) was stirred at 70° C. for 5 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-trifluoromethoxyphenyl)-piperazin-1-yl]phenol (1.95 g, yield 92%) as a white 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-f05195e35d65448abb920c592a1b992f
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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