반응 #411898

반응 방정식

toluene

4-morpholinoaniline

calcium chloride

aluminum chloride

→

title compound

수율 58.4%

bis(4-morpholinophenyl)amine

수율 58.4%

용매

—

ice water

decahydronaphthalene

반응 조건

후처리

1. 1
   기타The resulting mixture was reacted at 200 to 210° C. for 5 hours under a nitrogen atmosphere
2. 2
   온도After cooling
3. 3
   workup.STIRRINGThe resulting mixture was stirred
4. 4
   기타the resulting water layer was separated out
5. 5
   세척The organic layer was washed successively with 90 ml of a 5% aqueous solution of hydrochloric acid, 60 ml of a 5% aqueous solution of sodium bicarbonate and 60 ml of water
6. 6
   기타After removal of the organic solvent
7. 7
   workup.DISTILLATIONby distillation under reduced pressure, 48 ml of isopropyl alcohol
8. 8
   workup.ADDITIONwas added to the residue
9. 9
   기타the mixture was crystallized overnight at −3 to −8° C
10. 10
    여과The resulting crystals were collected by filtration
11. 11
    세척washed with 18 ml of isopropyl alcohol
12. 12
    기타dried

실험 절차

In a 300-ml four-necked flask were charged 68 ml of decahydronaphthalene (boiling point: 190° C.) as a solvent and 17.8 g (0.50 mol) of 4-morpholinoaniline, followed by the addition of 15.4 g (0.138 mol) of anhydrous calcium chloride and 18.5 g (0.138 mol) of anhydrous aluminum chloride under stirring. The resulting mixture was reacted at 200 to 210° C. for 5 hours under a nitrogen atmosphere. After cooling, the reaction mixture was added with 76 ml of toluene, followed by charging in 96 g of ice water. The resulting mixture was stirred and allowed to stand, and then, the resulting water layer was separated out. The organic layer was washed successively with 90 ml of a 5% aqueous solution of hydrochloric acid, 60 ml of a 5% aqueous solution of sodium bicarbonate and 60 ml of water. After removal of the organic solvent by distillation under reduced pressure, 48 ml of isopropyl alcohol was added to the residue and the mixture was crystallized overnight at −3 to −8° C. The resulting crystals were collected by filtration, washed with 18 ml of isopropyl alcohol and then dried, whereby 44.9 g (yield: 58.4%) of the title compound was obtained as white crystals. As a result of HPLC. analysis (column: YMC-A-312, detection UV: 280 nm, flow rate: 1.0 ml/min, eluent: acetonitrile/water 7/3), the compound was found to have a purity of 99.7%.

출처