반응 #451888

반응 방정식

2-nitroimidazole

NaH

4-bromomethyl-1-piperidinecarboxaldehyde

→

4[(2-nitro-1H-imidazol-1-yl)methyl]-1-piperidinecarboxaldehyde

수율 25.3%

용매

dimethylformamide

dimethylformamide

반응 조건

후처리

1. 1
   온도heated at 120° C. for 1/2 hr
2. 2
   기타After the reaction, solvent
3. 3
   기타was removed in vacuo and water (50 ml)
4. 4
   workup.ADDITIONwas added
5. 5
   추출the mixture was extracted with ethylacetate (2×75 ml)
6. 6
   건조The extracts, dried over Na2SO4
7. 7
   기타was then purified on silica gel column
8. 8
   세척eluted with 5% volume MeOH-95% volume CH2Cl2

실험 절차

The mixture of 2-nitroimidazole (4.5 g, 40 mM) and 50% by weight NaH in mineral oil (1.92 g, 41 mM) in dimethylformamide (40 ml) was stirred at room temperature for 1/2 hr. A solution of 4-bromomethyl-1-piperidinecarboxaldehyde (8.3 g, 40 mM) in dimethylformamide (10 ml) was added to the above mixture and heated at 120° C. for 1/2 hr. After the reaction, solvent was removed in vacuo and water (50 ml) was added and the mixture was extracted with ethylacetate (2×75 ml). The extracts, dried over Na2SO4 was stripped to dryness which was then purified on silica gel column, eluted with 5% volume MeOH-95% volume CH2Cl2, to give 4[(2-nitro-1H-imidazol-1-yl)methyl]-1-piperidinecarboxaldehyde (2.4 g, 10 mL) in 25% yield.

출처