Реакция #7237

Уравнение реакции

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

4-cyanobenzaldehyde

sodium triacetoxyborohydride

→

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

Выход 72.0%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   Другоеthe reaction was quenched with 1N NaOH (250 mL)
2. 2
   ДругоеThe phases were separated
3. 3
   Промывкаthe organic phase was washed once with brine (200 mL)
4. 4
   Сушкаdried (Na2SO4)
5. 5
   Концентрированиеconcentrated
6. 6
   ДругоеPurification of the crude material by flash chromatography on silica gel (5% CH3OH/CH2Cl2)

Методика

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.

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