Reaktion #2358535

Reaktionsgleichung

triethylamine

3-(5-dimethylcarbamoyl-pent-1-ynyl)-benzoic acid

EDCI

→

N-cyclopropyl-3-(5-dimethylcarbamoyl-pent-1-ynyl)benzamide

Ausbeute 91.0%

N-Cyclopropyl-3-(5-dimethylcarbamoyl-pent-1-ynyl)benzamide

Ausbeute 91.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONCyclopropyilamine (0.027 g, 0.38 mmol) was then added
2. 2
   workup.STIRRINGthe mixture stirred at room temperature for 16 hrs
3. 3
   WaschenThe reaction mixture was washed with a mixture of saturated brine and saturated sodium bicarbonate (1:1; 2×150 mL)
4. 4
   SonstigeThe organic layer was separated
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Sonstigethe solvent evaporated under vacuum
7. 7
   SonstigeThe residue was purified by flash column chromatography on silica gel (DCM:MeOH, 95% to 5% methanol gradient)

Vorschrift

To a solution of 3-(5-dimethylcarbamoyl-pent-1-ynyl)-benzoic acid (0.100 g, 0.38 mmol) in dry dichloromethane (1.5 mL) under a nitrogen atmosphere at room temperature, EDCI (0.0728 g, 0.38 mmol) was added followed by triethylamine (0.162 mL, 1.14 mmol), the resulting mixture was stirred at room temperature for further minutes. Cyclopropyilamine (0.027 g, 0.38 mmol) was then added and the mixture stirred at room temperature for 16 hrs. The reaction mixture was washed with a mixture of saturated brine and saturated sodium bicarbonate (1:1; 2×150 mL) followed by saturated brine solution (100 mL). The organic layer was separated and dried over magnesium sulfate and the solvent evaporated under vacuum. The residue was purified by flash column chromatography on silica gel (DCM:MeOH, 95% to 5% methanol gradient) to afford N-cyclopropyl-3-(5-dimethylcarbamoyl-pent-1-ynyl)benzamide (25) (0.10 g, 0.34 mmol, 91% yield).

Quelle