Triethylamine → [Benzo[b]thiophene-2-yl][1-(2-phenylethyl)-4-piperidinyl]methanone

HRID 266096

Reaktionsgleichung

C(Cl)(=O)C(Cl)=O.[C:7]1([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([CH:21]([C:23]3[S:27][C:26]4[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=4[CH:24]=3)[OH:22])[CH2:17][CH2:16]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>C(Cl)Cl.CS(C)=O>[S:27]1[C:23]([C:21]([CH:18]2[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:16][CH2:17]2)=[O:22])=[CH:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]1=2

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

Dissolve oxalyl chloride (4.22 g, 33.28 mmol) in methylene chloride (200 mL), place under an argon atmosphere and cool to -78° C. Add, by dropwise addition, dimethylsulfoxide (5.42 g, 69.33 mmol) and stir at -78° C. for 15 minutes. Add, by dropwise addition, a solution of α-[1-(2-phenylethyl)-4-piperidinyl]-2-benzo[b]thiophenemethanol (9.75 g, 27.73 mmol) in dimethylsulfoxide (150 mL). Stir at -78° C. for 30 minutes, add triethylamine (15.18 g, 0.150 mol) and stir at -78° C. for 1 hour. Remove the ice bath and stir for an additional 1.5 hours. Evaporate the solvent in vacuo and recrystallize (isopropanol) to give the title compound as a fluffy white crystalline solid; mp 129°-130° C.

Aufarbeitung

additionAdd, by dropwise addition
stirringStir at -78° C. for 30 minutes
stirringstir at -78° C. for 1 hour
customRemove the ice bath
stirringstir for an additional 1.5 hours
customEvaporate the solvent in vacuo
customrecrystallize (isopropanol)

Quellen und Nachweise

ORD-Eintrag: ord-1f16502ab5d54723934cdff55a1b4da9
Quelldatensatz: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05650416

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