반응 #423411

반응 방정식

ethyl 4-fluoro-3-nitrobenzoate

2-methylpiperidine

lithium hydroxide

→

title compound

수율 94.4%

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

수율 94.4%

용매

THF

DMF

water

water

반응 조건

후처리

1. 1
   기타to return to room temperature
2. 2
   추출Extraction with ethyl acetate
3. 3
   건조drying over sodium sulfate and concentration in vacuo
4. 4
   기타gave a yellow oil
5. 5
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 16 hours
6. 6
   기타After evaporation of the THF
7. 7
   workup.ADDITIONthe solution was diluted with water
8. 8
   세척washed with Et2O
9. 9
   추출extracted with Et2O
10. 10
    건조dried over magnesium sulfate
11. 11
    농축concentrated in vacuo

실험 절차

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.

출처