Benzo(B)Thiophene → alpha-[1-[2-(4-Methoxyphenyl)ethyl]-4-piperidinyl]-alpha-(benzo[b]thiophene-2-yl)-2-benzo[b]thiophenemethanol

HRID 266104

反応式

HRID 266104 の反応式
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2.[CH2:10]([Li])[CH2:11][CH2:12][CH3:13].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][CH:28]([C:31]([O:33]C)=O)[CH2:27][CH2:26]2)=[CH:19][CH:18]=1>O1CCCC1>[CH3:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][N:25]2[CH2:26][CH2:27][CH:28]([C:31]([C:10]3[S:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:13][C:12]=4[CH:11]=3)([C:5]3[S:1][C:2]4[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=4[CH:4]=3)[OH:33])[CH2:29][CH2:30]2)=[CH:21][CH:22]=1

参加物

5

反応物 3

HCID 7221Benzo(B)ThiopheneHCID 108695871-[2-(4-Methoxyphenyl)ethyl]-4-piperidinecarboxylic acid, methyl esterHCID 178418339Butyllithium

生成物 1

HCID 18930359alpha-[1-[2-(4-Methoxyphenyl)ethyl]-4-piperidinyl]-alpha-(benzo[b]thiophene-2-yl)-2-benzo[b]thiophenemethanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

Dissolve benzo[b]thiophene (10.0 g, 74.5 mmol) in anhydrous tetrahydrofuran (100 mL), place under an argon atmosphere and cool to -78° C. Add, by dropwise addition, n-butyllithium (32.79 mL, 81.97 mmol) and stir briefly. Add, by dropwise addition, a solution of 1-[2-(4-methoxyphenyl)ethyl]-4-piperidinecarboxylic acid, methyl ester (20.67 g, 74.52 mmol) in anhydrous tetrahydrofuran (200 mL) and stir at -78° C. for 1.5 hours. Quench with saturated ammonium chloride, separate the organic phase and extract the aqueous phase with ethyl ether. Combine the organic phases, dry (MgSO4) and evaporate the solvent in vacuo. Purify by chromatography (50% ethyl acetate/hexane) and recrystallize (isopropanol) to give the title compound as a white solid; mp 168°-179° C.

後処理

  1. additionAdd, by dropwise addition
  2. customQuench with saturated ammonium chloride
  3. customseparate the organic phase
  4. extractionextract the aqueous phase with ethyl ether
  5. dry with materialdry (MgSO4)
  6. customevaporate the solvent in vacuo
  7. customPurify by chromatography (50% ethyl acetate/hexane)
  8. customrecrystallize (isopropanol)

出典と根拠

ORDレコード
ord-be7ebf8fca914435a43f72ed005540df
出典データセット
uspto-grants-1997_07
特許番号
US05650416

関連ノート

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