Réaction #7237

Équation de réaction

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

4-cyanobenzaldehyde

sodium triacetoxyborohydride

→

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

Rendement 72.0%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Autrethe reaction was quenched with 1N NaOH (250 mL)
2. 2
   AutreThe phases were separated
3. 3
   Lavagethe organic phase was washed once with brine (200 mL)
4. 4
   Séchagedried (Na2SO4)
5. 5
   Concentrationconcentrated
6. 6
   AutrePurification of the crude material by flash chromatography on silica gel (5% CH3OH/CH2Cl2)

Mode opératoire

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.

Source