Reaction #2832

Reaction equation

3-nitrobenzoic acid

1-hydroxybenzotriazole

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

morpholine

→

compound ( [13]-(132)-158 )

Yield 89.8%

3-nitrobenzoic acid morpholide

Yield 89.8%

Solvents

tetrahydrofuran

dichloromethane

chloroform

Conditions

Workup

1. 1
   WashThe mixture was washed with 1N-HCl aqueous solution, 1N-NaOH aqueous solution
2. 2
   workup.DISTILLATIONdistilled water
3. 3
   DryingThe organic layer was dried over anhydrous sodium sulfate
4. 4
   OtherThe solvent was evaporated under reduced pressure
5. 5
   Otherthe residue was purified by silica gel column chromatography (Kieselgel 60=160 g, ethyl acetate)

Procedure

In tetrahydrofuran (100 ml) and dichloromethane (100 ml), 3-nitrobenzoic acid (7.58 g) was dissolved. Then 1-hydroxybenzotriazole (6.74 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (9.57 g), and morpholine (9.47 g) were added to the solution. The mixture was stirred at room temperature overnight. After the reaction was completed, chloroform was added to the solution. The mixture was washed with 1N-HCl aqueous solution, 1N-NaOH aqueous solution, and distilled water. The organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (Kieselgel 60=160 g, ethyl acetate) to obtain the above-captioned compound ([13]-(132)-158) (9.62 g) as white crystals.

Source