反応 #155336

反応方程式

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

収率 41.3%

溶媒

acetonitrile

acetonitrile

反応条件

後処理

1. 1
   濃縮The resulting mixture was concentrated under reduced pressure
2. 2
   抽出the residue was subjected to extraction
3. 3
   洗浄The extract was then sequentially washed with water
4. 4
   濃縮The washed product was concentrated under reduced pressure
5. 5
   その他the residue was purified
6. 6
   濃縮The 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
    濃縮the mixture was concentrated to dryness under reduced pressure

実験手順

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).

出典