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

HRID 856100노트

반응식

HRID 856100 반응식
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

참가 물질

4

반응물 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 230811991-[4-(Tetrahydropyran-2-yloxy)phenyl]-4-(4-trifluoromethoxyphenyl)piperazine

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f05195e35d65448abb920c592a1b992f
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262212B2

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