Reacción #7237

Ecuación de reacción

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

4-cyanobenzaldehyde

sodium triacetoxyborohydride

→

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

Rendimiento 72.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction was quenched with 1N NaOH (250 mL)
2. 2
   OtroThe phases were separated
3. 3
   Lavadothe organic phase was washed once with brine (200 mL)
4. 4
   Secadodried (Na2SO4)
5. 5
   Concentraciónconcentrated
6. 6
   OtroPurification of the crude material by flash chromatography on silica gel (5% CH3OH/CH2Cl2)

Procedimiento

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.

Fuente