反应 #50513

反应方程式

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

triethylamine

4-pyridinecarboxaldehyde

→

powder

收率 60.7%

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

收率 60.7%

溶剂

methanol

反应条件

后处理

1. 1
   温度was refluxed for 30 minutes
2. 2
   其他The volatiles were evaporated
3. 3
   其他the crude product was partitioned between water and dichloromethane
4. 4
   洗涤The organic layer was washed with brine
5. 5
   干燥dried over magnesium sulfate
6. 6
   过滤filtered
7. 7
   浓缩concentrated
8. 8
   workup.DISSOLUTIONThe crude material was immediately dissolved in methanol (10 ml)
9. 9
   workup.ADDITIONwas added sodium borohydride (168 mg)
10. 10
    其他normal extractive workup afforded a yellow foam, which
11. 11
    其他was purified by column chromatography
12. 12
    其他The product was recrystallized from hexane-ethyl acetate

实验过程

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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