1,2-Dichloroethane → N'-cyclooctyl-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine

Beteiligte Stoffe

Reaktionsschritte

254 mg Cyclooctylamine and 434 mg 4-dimethylamino-4-phenyl-cyclohexanone were dissolved in dry tetrahydrofuran (15 ml) and 1,2-dichloroethane (5 ml) under argon. Glacial acetic acid (120 mg) and 600 mg sodium triacetoxyborohydride were added to this mixture and the mixture was stirred for 18 hours at RT. For working up, the reaction mixture was concentrated and the residue was washed with one molar hydrochloric acid (20 ml) and with ether (2×30 ml). The aqueous phase was rendered alkaline with five molar sodium hydroxide solution and extracted with ether (3×30 ml). The combined extracts were dried over sodium sulfate and filtered and the filtrate was concentrated. The crude product (515 mg) was chromatographed over silica gel with methanol. 108 mg N′-cyclooctyl-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine were obtained as a colorless oil, from which the corresponding dihydrochloride was precipitated with 3.3 M ethanolic hydrochloric acid (0.25 ml) in 2-butanone (2 ml) (102 mg; m.p. 247-249° C.).

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