Reaktion #50513

Reaktionsgleichung

1,3-dihydro-1-(4-morpholinyl)-2H-indol-2-one

triethylamine

4-pyridinecarboxaldehyde

→

powder

Ausbeute 60.7%

1,3-dihydro-1-(4-morpholinyl)-3-(4-pyridinylmethyl )-2H-indol-2-one

Ausbeute 60.7%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 30 minutes
2. 2
   SonstigeThe volatiles were evaporated
3. 3
   Sonstigethe crude product was partitioned between water and dichloromethane
4. 4
   WaschenThe organic layer was washed with brine
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   workup.DISSOLUTIONThe crude material was immediately dissolved in methanol (10 ml)
9. 9
   workup.ADDITIONwas added sodium borohydride (168 mg)
10. 10
    Sonstigenormal extractive workup afforded a yellow foam, which
11. 11
    Sonstigewas purified by column chromatography
12. 12
    SonstigeThe product was recrystallized from hexane-ethyl acetate

Vorschrift

A mixture of 1,3-dihydro-1-(4-morpholinyl)-2H-indol-2-one (301 mg, 1.38 mmole), triethylamine (0.22 ml, 1.52 mmole) , 4-pyridinecarboxaldehyde (0.15 ml, 1.52 mmole) in methanol (3 ml) was refluxed for 30 minutes. The volatiles were evaporated and the crude product was partitioned between water and dichloromethane. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude red oil was characterized by mass spec., m/e 308 (M+H, 100%) for the aldol/dehydration product. The crude material was immediately dissolved in methanol (10 ml), cooled to 0° C., to which was added sodium borohydride (168 mg). After stirring 30 minutes, normal extractive workup afforded a yellow foam, which was purified by column chromatography using 5% methanol-chloroform. The product was recrystallized from hexane-ethyl acetate to give 259 mg of a powder, m.p. 108°-110° C. Anal (C18H19N3O2): C,H,N.

Quelle