تفاعل #7237

معادلة التفاعل

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

4-cyanobenzaldehyde

sodium triacetoxyborohydride

→

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

المردود 72.0%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   أخرىthe reaction was quenched with 1N NaOH (250 mL)
2. 2
   أخرىThe phases were separated
3. 3
   غسيلthe organic phase was washed once with brine (200 mL)
4. 4
   تجفيفdried (Na2SO4)
5. 5
   تركيزconcentrated
6. 6
   أخرىPurification of the crude material by flash chromatography on silica gel (5% CH3OH/CH2Cl2)

الإجراء التجريبي

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.

المصدر