Sodium Bicarbonate → 2-[4-(4-Trifluoromethylphenyl)piperazin-1-yl]methyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole

To a solution of 2-chloro-4-nitro-1H-imidazole (1.59 g, 10.8 mmol) and 1-(2-methyloxiran-2-ylmethyl)-4-(4-trifluoromethylphenyl)piperazine (3.23 g, 10.8 mmol) in 1-propanol (20 ml), sodium hydrogencarbonate (1.95 g, 23.8 mmol) was added followed by stirring under reflux overnight. The reaction mixture was concentrated under reduced pressure. The residue was added water, and the solution was extracted with methylene chloride. The organic phase was dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1) and crystallized from methylene chloride-isopropyl ether to afford 2-[4-(4-trifluoromethylphenyl)piperazin-1-yl]methyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole (1.34 g, yield 29%) as a a light yellow powder.

1. temperatureunder reflux overnight
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. additionThe residue was added water
4. extractionthe solution was extracted with methylene chloride
5. dry with materialThe organic phase was dried over sodium sulfate
6. filtrationfiltered
7. concentrationThe filtrate was concentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1)
9. customcrystallized from methylene chloride-isopropyl ether

ORD 기록

ord-41a7f8589a42425f9f35d1d43065d48a

출처 데이터셋

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07262212B2