Acetic Acid → HCID 10156762, compound

Participants

Reaction Steps

1-Aminofluorene (181 mg, 1 mmol) and 4-dimethylamino-4-phenylcyclohexanone (217 mg, 1 mmol) were dissolved in dry 1,2-dichloroethane (10 ml) under argon. Glacial acetic acid (1 mmol) and sodium triacetoxyborohydride (300 mg) were added to this mixture and the mixture was stirred for 24 hours at RT. For working up, the mixture was concentrated and the residue was adjusted to pH 11 with five molar sodium hydroxide solution. The alkaline phase was diluted with water (10 ml) and extracted with ethyl acetate (4×20 ml). The combined extracts were dried over sodium sulfate and filtered and the filtrate was concentrated. The crude product was chromatographed over silica gel with ethyl acetate/ethanol (1:1). 200 mg N′-(9H-fluoren-1-yl)-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine were obtained as a colorless oil, which, for preparation of the hydrochloride, was dissolved in 2-butanone (5 ml), and 1.85 M ethanolic HCl (0.7 ml) was added. The N′-(9H-fluoren-1-yl)-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine dihydrochloride obtained was filtered off with suction and dried (220 mg, m.p. 223-225° C.).

Provenance & Evidence