반응 #155336

반응 방정식

1-(2-Methoxyethyl)piperazine

triethylamine

2-Chloro-N-{3-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]propyl}acetamide

→

N-{3-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]propyl}-2-[4-(2-methoxyethyl)piperazin-1-yl]acetamide hydrochloride

수율 41.3%

용매

acetonitrile

acetonitrile

반응 조건

후처리

1. 1
   농축The resulting mixture was concentrated under reduced pressure
2. 2
   추출the residue was subjected to extraction
3. 3
   세척The extract was then sequentially washed with water
4. 4
   농축The washed product was concentrated under reduced pressure
5. 5
   기타the residue was purified
6. 6
   농축The purified product was concentrated under reduced pressure
7. 7
   workup.DISSOLUTIONthe residue was then dissolved in ethyl acetate (5 ml)
8. 8
   workup.ADDITIONA 4N hydrogen chloride ethyl acetate solution (0.19 ml) was added
9. 9
   workup.STIRRINGstirred
10. 10
    농축the mixture was concentrated to dryness under reduced pressure

실험 절차

2-Chloro-N-{3-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]propyl}acetamide (370 mg, 0.8 mmol) was suspended in acetonitrile (12 ml). 1-(2-Methoxyethyl)piperazine (138 mg, 0.96 mmol), triethylamine (162 mg, 1.6 mmol) and acetonitrile (2 ml) were added to the suspension, and stirred at 70 to 80° C. for 6 hours. The resulting mixture was concentrated under reduced pressure, and the residue was subjected to extraction using ethyl acetate. The extract was then sequentially washed with water, an aqueous saturated sodium chloride solution, and an aqueous saturated sodium bicarbonate solution. The washed product was concentrated under reduced pressure, and the residue was purified using silica gel column chromatography (dichloromethane:methanol=30:1→10:1). The purified product was concentrated under reduced pressure, and the residue was then dissolved in ethyl acetate (5 ml). A 4N hydrogen chloride ethyl acetate solution (0.19 ml) was added thereto and stirred, and then the mixture was concentrated to dryness under reduced pressure, giving a pale yellow amorphous solid of N-{3-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]propyl}-2-[4-(2-methoxyethyl)piperazin-1-yl]acetamide hydrochloride (200 mg).

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