Reaktion #7237

Reaktionsgleichung

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

4-cyanobenzaldehyde

sodium triacetoxyborohydride

→

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

Ausbeute 72.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction was quenched with 1N NaOH (250 mL)
2. 2
   SonstigeThe phases were separated
3. 3
   Waschenthe organic phase was washed once with brine (200 mL)
4. 4
   Trocknendried (Na2SO4)
5. 5
   Einengenconcentrated
6. 6
   SonstigePurification of the crude material by flash chromatography on silica gel (5% CH3OH/CH2Cl2)

Vorschrift

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.

Quelle