Reaktion #2823

Reaktionsgleichung

Morpholine

3-nitro-4-valeramidobenzoic acid

Dicyclohexylcarbodiimide

1-hydroxybenzotriazole

→

3-nitro-4-valeramidobenzoic acid morpholide

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle