反应 #7237

反应方程式

8-amino-5,6,7,8-tetrahydroquinoline

4-cyanobenzaldehyde

sodium triacetoxyborohydride

→

N-(5,6,7,8-tetrahydro-8-quinolinyl)-4-cyanobenzylamine

收率 72.0%

溶剂

dichloromethane

反应条件

后处理

1. 1
   其他the reaction was quenched with 1N NaOH (250 mL)
2. 2
   其他The phases were separated
3. 3
   洗涤the organic phase was washed once with brine (200 mL)
4. 4
   干燥dried (Na2SO4)
5. 5
   浓缩concentrated
6. 6
   其他Purification of the crude material by flash chromatography on silica gel (5% CH3OH/CH2Cl2)

实验过程

To a stirred solution of 8-amino-5,6,7,8-tetrahydroquinoline (24.3 g, 164 mmol) in dichloromethane (600 mL), at room temperature, was added 4-cyanobenzaldehyde (21.5 g, 164 mmol) and sodium triacetoxyborohydride (45 g, 210 mmol). After 42 hours, the reaction was quenched with 1N NaOH (250 mL). The phases were separated and the organic phase was washed once with brine (200 mL), dried (Na2SO4), and concentrated. Purification of the crude material by flash chromatography on silica gel (5% CH3OH/CH2Cl2) provided 30.9 g (72%) of N-(5,6,7,8-tetrahydro-8-quinolinyl)-4-cyanobenzylamine as a pale yellow solid.

来源