반응 #50513

반응 방정식

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

triethylamine

4-pyridinecarboxaldehyde

→

powder

수율 60.7%

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

수율 60.7%

용매

methanol

반응 조건

후처리

1. 1
   온도was refluxed for 30 minutes
2. 2
   기타The volatiles were evaporated
3. 3
   기타the crude product was partitioned between water and dichloromethane
4. 4
   세척The organic layer was washed with brine
5. 5
   건조dried over magnesium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   workup.DISSOLUTIONThe crude material was immediately dissolved in methanol (10 ml)
9. 9
   workup.ADDITIONwas added sodium borohydride (168 mg)
10. 10
    기타normal extractive workup afforded a yellow foam, which
11. 11
    기타was purified by column chromatography
12. 12
    기타The product was recrystallized from hexane-ethyl acetate

실험 절차

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.

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