反応 #7237

反応方程式

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

4-cyanobenzaldehyde

sodium triacetoxyborohydride

→

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

収率 72.0%

溶媒

dichloromethane

反応条件

後処理

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

実験手順

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.

出典