Reacción #2823

Ecuación de reacción

Morpholine

3-nitro-4-valeramidobenzoic acid

Dicyclohexylcarbodiimide

1-hydroxybenzotriazole

→

3-nitro-4-valeramidobenzoic acid morpholide

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was stirred for 16 hours
2. 2
   OtroAfter the insolubles were removed from the reaction solution
3. 3
   Concentraciónthe solution was concentrated
4. 4
   Otrodried
5. 5
   workup.DISSOLUTIONThe crude product was dissolved in chloroform
6. 6
   Otrothe insolubles were removed
7. 7
   Otrothe solution was purified by silica gel column chromatography (Kieselgel 60=400 g, chloroform/methanol=30/1)
8. 8
   Otroto obtain the compound ([1]-(12)-1) (22.95 g) as yellow needle crystals

Procedimiento

In tetrahydrofuran (800 ml), 3-nitro-4-valeramidobenzoic acid ([1]-(11)-1) (20.0 g) was dissolved. Dicyclohexylcarbodiimide (17.1 g) and 1-hydroxybenzotriazole (11.2 g) were added to the solution, and the mixture was stirred at room temperature for 15 minutes. Morpholine (7.27 g) was further added to the solution. The mixture was stirred for 16 hours. After the insolubles were removed from the reaction solution, the solution was concentrated and dried. The crude product was dissolved in chloroform, and the insolubles were removed, and the solution was purified by silica gel column chromatography (Kieselgel 60=400 g, chloroform/methanol=30/1) to obtain the compound ([1]-(12)-1) (22.95 g) as yellow needle crystals.

Fuente