反应 #2320164

反应方程式

2-Chloro-nicotinonitrile

[1,4]Diazepane-1-carboxylic acid tert-butyl ester

potassium hydogencarbonate

→

4-(2-Cyano-phenyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

溶剂

N,N-dimethylformamide

反应条件

后处理

1. 1
   workup.ADDITIONThe reaction mixture was poured onto ice
2. 2
   萃取extracted with dichloromethane
3. 3
   洗涤The organic layer was washed with water and brine
4. 4
   干燥then dried over magnesium sulfate
5. 5
   过滤filtered
6. 6
   其他The solvent was removed
7. 7
   其他the residue was purified by flash column chromatography on silica

实验过程

2-Chloro-nicotinonitrile(1.0 g, 7.215 mmol) was added to a mixture of [1,4]Diazepane-1-carboxylic acid tert-butyl ester and potassium hydogencarbonate (0.87 g, 8.66 mmol) in N,N-dimethylformamide (20 mL). The mixture was heated at 90° C. overnight. The reaction mixture was poured onto ice and extracted with dichloromethane. The organic layer was washed with water and brine then dried over magnesium sulfate and filtered. The solvent was removed and the residue was purified by flash column chromatography on silica using ethyl acetate/heptane (50:50) mixture as the mobile phase to give 4-(2-Cyano-phenyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester. 1H-NMR (400 MHz, DMSO-d6) δ 1.25 (d, 27 Hz, 9H), 1.81 (m, 1H), 1.87 (m, 1H), 3.31 (m, 2H), 3.55(m,1H), 3.60 (m,1H), 3.84 (m, 2H), 3.94 (m, 2H), 6.75 (m,2H), 8.34 (m,1H).

来源