反应详情

292 mg C-(1H-indol-3-yl)methylamine were dissolved in dry 1,2-dichloroethane (15 ml) and THF (5 ml) under argon to give an almost clear solution. After addition of 4-dimethylamino-4-phenylcyclohexanone (435 mg), glacial acetic acid (4 mmol) and sodium triacetoxyborohydride (550 mg), a suspension was present, which was stirred for 72 hours at RT. For working up, water (20 ml) was added to the reaction mixture and the mixture was stirred vigorously for one hour. The organic phase was separated off and the aqueous phase was extracted twice with ether (10 ml) and then rendered strongly alkaline with five molar sodium hydroxide solution. The aqueous phase was extracted with ethyl acetate (4×10 ml). A solid, which dissolved in ethyl acetate (50 ml) with warming, thereby precipitated out. The combined extracts were dried over sodium sulfate and filtered and the filtrate was concentrated. The crude product obtained (382 mg) was recrystallized from a mixture of ethanol (1 ml) and ethyl acetate (5 ml). The precipitate was filtered off with suction and washed with a little cold ethyl acetate. 156 mg N′-(1H-indol-3-ylmethyl)-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine were obtained as a cis/trans mixture.

1. stirringthe mixture was stirred vigorously for one hour
2. customThe organic phase was separated off
3. extractionthe aqueous phase was extracted twice with ether (10 ml)
4. extractionThe aqueous phase was extracted with ethyl acetate (4×10 ml)
5. dissolutionA solid, which dissolved in ethyl acetate (50 ml)
6. temperaturewith warming
7. customprecipitated out
8. dry with materialThe combined extracts were dried over sodium sulfate
9. filtrationfiltered
10. concentrationthe filtrate was concentrated
11. customThe crude product obtained (382 mg)
12. customwas recrystallized from a mixture of ethanol (1 ml) and ethyl acetate (5 ml)
13. filtrationThe precipitate was filtered off with suction
14. washwashed with a little cold ethyl acetate