Réaction #156194

Équation de réaction

2-(2-{[3-(4-Bromophenoxy)propyl]pyridin-4-ylmethylamino}ethyl)-2H-isoquinolin-1-one

2-pyrrolidone

potassium carbonate

N,N′-dimethyl ethylenediamine

hydrochloric acid

→

title compound

2-[2-({3-[4-(2-oxopyrrolidin-1-yl)phenoxy]propyl}pyridin-4-ylmethylamino)ethyl]-2H-isoquinolin-1-one dihydrochloride

Solvants

ethanol

toluene

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was cooled to room temperature
2. 2
   workup.ADDITIONAfter adding aqueous
3. 3
   Extractionammonia, extraction
4. 4
   LavageThe organic layer was washed with saturated saline
5. 5
   Séchagedried with sodium sulfate
6. 6
   Autrecondensed under reduced pressure
7. 7
   Autrethe residue was purified by silica gel column chromatography (ethyl acetate:methanol=100:0,70:30)
8. 8
   Autrecondensed under reduced pressure
9. 9
   Autrefollowed by condensation under reduced pressure
10. 10
    AutreThe residue was recrystallized from isopropyl alcohol/water

Mode opératoire

2-(2-{[3-(4-Bromophenoxy)propyl]pyridin-4-ylmethylamino}ethyl)-2H-isoquinolin-1-one (500 mg), 2-pyrrolidone (0.228 ml), potassium carbonate (415 mg), copper iodide (I)(190 mg), and N,N′-dimethyl ethylenediamine (0.39 ml) were added to toluene (5 ml). The mixture was stirred at 100° C. for 12 hours under nitrogen atmosphere. The reaction mixture was cooled to room temperature. After adding aqueous ammonia, extraction was performed using ethyl acetate. The organic layer was washed with saturated saline, and dried with sodium sulfate. After the organic layer was condensed under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate:methanol=100:0,70:30). The purified product was condensed under reduced pressure. A condensed hydrochloric acid (0.3 ml) was added to an ethanol solution of the residue, followed by condensation under reduced pressure. The residue was recrystallized from isopropyl alcohol/water to give the title compound (350 mg) as a white powder. mp: 210 to 214° C. (dec.)

Source