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

HRID 856100ノート

反応式

HRID 856100 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f05195e35d65448abb920c592a1b992f
出典データセット
uspto-grants-2007_08
特許番号
US07262212B2

反応ノート

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