反応 #423411

反応方程式

ethyl 4-fluoro-3-nitrobenzoate

2-methylpiperidine

lithium hydroxide

→

title compound

収率 94.4%

4-(2-Methylpiperidin-1-yl)-3-nitrobenzoic acid

収率 94.4%

溶媒

THF

DMF

water

water

反応条件

後処理

1. 1
   その他to return to room temperature
2. 2
   抽出Extraction with ethyl acetate
3. 3
   乾燥drying over sodium sulfate and concentration in vacuo
4. 4
   その他gave a yellow oil
5. 5
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 16 hours
6. 6
   その他After evaporation of the THF
7. 7
   workup.ADDITIONthe solution was diluted with water
8. 8
   洗浄washed with Et2O
9. 9
   抽出extracted with Et2O
10. 10
    乾燥dried over magnesium sulfate
11. 11
    濃縮concentrated in vacuo

実験手順

A mixture of ethyl 4-fluoro-3-nitrobenzoate (Chontech 01072; 1.00 g; 4.69 mmol; 1 eq.) and 2-methylpiperidine (Aldrich M7, 280-3; 1.396 g; 14.07 mmol; 3 eq.) in DMF (4 mL) was stirred at 50° C. for 3 hours. The reaction was then allowed to return to room temperature and diluted with water. Extraction with ethyl acetate, drying over sodium sulfate and concentration in vacuo gave a yellow oil. The oil was taken up in THF (10 mL) and lithium hydroxide (561.73 mg; 23.46 mmol; 5 eq.) was added followed by water (10 mL). The reaction mixture was stirred at room temperature for 16 hours. After evaporation of the THF, the solution was diluted with water and washed with Et2O. The aqueous layer was acidified to pH 5 with AcOH, extracted with Et2O, dried over magnesium sulfate and concentrated in vacuo to afford the title compound (1.17 g, 94%) as a yellow solid.

出典