Water → N-(1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-azetidinyl)acetamide

HRID 562385

Reaktionsgleichung

Cl[CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]2[S:15][CH:14]=[CH:13][C:12]=2[CH:16]=1.[NH:17]1[CH2:20][CH:19]([NH:21][C:22](=[O:24])[CH3:23])[CH2:18]1.O.C(OCC)(=O)C>CN(C)C=O>[S:15]1[C:11]2[CH:10]=[CH:9][C:8]([CH2:7][CH2:6][O:5][CH2:4][CH2:3][CH2:2][N:17]3[CH2:20][CH:19]([NH:21][C:22](=[O:24])[CH3:23])[CH2:18]3)=[CH:16][C:12]=2[CH:13]=[CH:14]1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

0.80 g of 5-(2-(3-chloropropoxy)ethyl)-1-benzothiophene was dissolved in 8 ml of N,N-dimethylformamide. Thereafter, 1.20 g of N-(3-azetidinyl)acetamide was added to the obtained solution, and the obtained mixture was stirred at 90° C. for 12 hours. After cooling, water and ethyl acetate were added to the reaction mixture, and an organic layer was separated. The organic layer was successively washed with water and a saturated saline solution, and then dried over anhydrous magnesium sulfate. Thereafter, the solvent was distilled away under a reduced pressure. The residue was purified by column chromatography (eluent; chloroform:methanol=7:1), so as to obtain 0.39 g of a light yellow oil product, N-(1-(3-(2-(1-benzothiophene-5-yl)ethoxy)propyl)-3-azetidinyl)acetamide.

Aufarbeitung

temperatureAfter cooling
customan organic layer was separated
washThe organic layer was successively washed with water
dry with materiala saturated saline solution, and then dried over anhydrous magnesium sulfate
distillationThereafter, the solvent was distilled away under a reduced pressure
customThe residue was purified by column chromatography (eluent; chloroform:methanol=7:1)

Quellen und Nachweise

ORD-Eintrag: ord-d06c4b5c118a48db8753c609d92c963b
Quelldatensatz: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08067406B2

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