반응 #7237

반응 방정식

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

4-cyanobenzaldehyde

sodium triacetoxyborohydride

→

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

수율 72.0%

용매

dichloromethane

반응 조건

후처리

1. 1
   기타the reaction was quenched with 1N NaOH (250 mL)
2. 2
   기타The phases were separated
3. 3
   세척the organic phase was washed once with brine (200 mL)
4. 4
   건조dried (Na2SO4)
5. 5
   농축concentrated
6. 6
   기타Purification of the crude material by flash chromatography on silica gel (5% CH3OH/CH2Cl2)

실험 절차

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.

출처