Water → (RS)-1-[1-(acenaphthen-1-yl)piperidin-4-yl]-1,3-dihydro-3-methyl-2H-benzoimidazole-2-thione

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Reaktionsgleichung

[CH:1]1([N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[NH:21][C:20]3=[S:28])[CH2:15][CH2:14]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[CH2:2]1.[H-].[Na+].[CH3:31]I.O>CN(C=O)C>[CH:1]1([N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21]([CH3:31])[C:20]3=[S:28])[CH2:15][CH2:14]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[CH2:2]1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

(RS)-1-[1-(Acenaphthen-1-yl)piperidin-4-yl]-1,3-dihydro-2H-benzoimidazole-2-thione (1 g, 2.6 mmol) was dissolved in DMF (15 ml) and sodium hydride (120 mg, 60%) was added. The suspension was stirred at 50° C. for 30 min. After cooling to room temperature, methyl iodide (0.4 g, 2.8 mmol) was added and the mixture was stirred for 1 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated aqueous ammonium chloride solution, dried over magnesium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (chloroform/methanol) to give the title compound (1.05 g) as pale-yellow crystals.

Aufarbeitung

temperatureAfter cooling to room temperature
stirringthe mixture was stirred for 1 hr
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with water and saturated aqueous ammonium chloride solution
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

Quellen und Nachweise

ORD-Eintrag: ord-9ba9f6d848c14660afe72f7039096ffc
Quelldatensatz: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07566728B2

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