Реакция #1267675

Уравнение реакции

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

Растворители

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe reaction mixture is stirred for 4 hours
2. 2
   Экстракцияextracted 2× with ethyl acetate
3. 3
   ПромывкаThe combined organic layers are washed sequentially with brine, aqueous 2N hydrochloric acid
4. 4
   Сушкаbrine, dried over sodium sulfate
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated in vacuo
7. 7
   workup.ADDITIONTo the residue is added 15% aqueous potassium bicarbonate (5 mL) and methyl alcohol (3 mL)
8. 8
   Температураheated
9. 9
   Температураat reflux for 3 hours
10. 10
    ТемператураAfter cooling
11. 11
    Экстракцияthe reaction mixture is extracted with ethyl acetate
12. 12
    Сушкаthe organic layer dried over sodium sulfate
13. 13
    Фильтрацияfiltered
14. 14
    Концентрированиеconcentrated in vacuo

Методика

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.

Источник