반응 #439085

반응 방정식

N-trifluoroacetyl-(methylaminomethyl)aniline

ammonium chloride

4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid

triethylamine

ethyl chloroformate

→

N[3-(methylaminomethyl)phenyl]-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxamide

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction mixture is stirred for 4 hours
2. 2
   추출extracted 2× with ethyl acetate
3. 3
   세척The combined organic layers are washed sequentially with brine, aqueous 2N hydrochloric acid
4. 4
   건조brine, dried over sodium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   workup.ADDITIONTo the residue is added 15% aqueous potassium bicarbonate (5 mL) and methyl alcohol (3 mL)
8. 8
   온도heated
9. 9
   온도at reflux for 3 hours
10. 10
    온도After cooling
11. 11
    추출the reaction mixture is extracted with ethyl acetate
12. 12
    건조the organic layer dried over sodium sulfate
13. 13
    여과filtered
14. 14
    농축concentrated in vacuo

실험 절차

To a stirred solution of 4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (100 mg, 0.6 mmol) and triethylamine (0.15 mL, 1.1 mmol) in N,N-dimethylformamide (5 mL) at 0° C. is added ethyl chloroformate (0.1 mL, 1.1 mmol). After stirring an additional 1 hour, 3-(N-trifluoroacetyl-(methylaminomethyl)aniline (0.3 g, 1.3 mmol) is added. The reaction mixture is stirred for 4 hours, then poured into saturated aqueous ammonium chloride and extracted 2× with ethyl acetate. The combined organic layers are washed sequentially with brine, aqueous 2N hydrochloric acid, then brine, dried over sodium sulfate, filtered, and concentrated in vacuo. To the residue is added 15% aqueous potassium bicarbonate (5 mL) and methyl alcohol (3 mL), then heated at reflux for 3 hours. After cooling, the reaction mixture is extracted with ethyl acetate, the organic layer dried over sodium sulfate, filtered, and concentrated in vacuo to give N[3-(methylaminomethyl)phenyl]-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxamide. m.p. 130-132° C.

출처