Reaktion #409814

Reaktionsgleichung

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

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITThe reaction mixture is stirrred for 4 hours
2. 2
   Extraktionextracted 2× with ethyl acetate
3. 3
   WaschenThe combined organic layers are washed sequentially with brine, aqueous 2N hydrochloric acid
4. 4
   Trocknenbrine, dried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo
7. 7
   workup.ADDITIONTo the residue is added 15% aqueous potassium bicarbonate (5 mL) and methyl alcohol (3 mL)
8. 8
   Temperaturheated
9. 9
   Temperaturat reflux for 3 hours
10. 10
    TemperaturAfter cooling
11. 11
    Extraktionthe reaction mixture is extracted with ethyl acetate
12. 12
    Trocknenthe organic layer dried over sodium sulfate
13. 13
    Filtrationfiltered
14. 14
    Einengenconcentrated in vacuo

Vorschrift

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 stirrred 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; (Compound 1) m.p. 130-132° C.

Quelle