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

HRID 266104

Reaktionsgleichung

Reaktionsgleichung von HRID 266104
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-be7ebf8fca914435a43f72ed005540df
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05650416

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