反応 #1266237

反応方程式

9-Aminofluorene

4-dimethylamino-4-phenylcyclohexanone

acetic acid

sodium triacetoxyborohydride

→

N′-(9H-fluoren-9-yl)-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine

収率 57.5%

溶媒

1,2-dichloroethane

反応条件

後処理

1. 1
   濃縮the mixture was concentrated
2. 2
   workup.ADDITIONThe alkaline phase was diluted with water (10 ml)
3. 3
   抽出extracted with ethyl acetate (5×20 ml)
4. 4
   乾燥The combined extracts were dried over sodium sulfate
5. 5
   ろ過filtered
6. 6
   濃縮the filtrate was concentrated
7. 7
   その他The crude product was chromatographed over silica gel with ethyl acetate/ethanol (1:1)

実験手順

9-Aminofluorene (362 mg, 2 mmol) and 4-dimethylamino-4-phenylcyclohexanone (434 mg, 2 mmol) were dissolved in dry 1,2-dichloroethane (10 ml) under argon. Glacial acetic acid (2 mmol) and sodium triacetoxyborohydride (600 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 (5×20 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). 440 mg N′-(9H-fluoren-9-yl)-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine were obtained as a white solid which, for preparation of the hydrochloride, was dissolved in 2-butanone (10 ml), and 1.85 M ethanolic HCl (1.55 ml) was added. The mixture of N′-(9H-fluoren-9-yl)-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine dihydrochloride obtained was filtered off with suction and dried (460 mg, m.p. 202-205° C.).

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