Sodium Hydroxide → 1-butyl-N,N-dimethyl-4,4-bis(3-methyl-5-(trifluoromethyl)-1H-indol-2-yl)cyclohexanamine

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Reaction Steps

4-butyl-4-(dimethylamino)cyclohexanone (395 mg, 2 mmol, synthesis cf. WO2008009415, ketone unit Ket-4) together with 3-methyl-5-trifluoromethyl-1H-indole (398 mg, 2 mmol, synthesis cf. WO2008009415, indole unit Ind-7) was dissolved in dichloromethane (20 ml). Trifluoromethane sulphonic acid (0.2 ml, 338 mg, 2.25 mmol) was then added. This was stirred for 3 d at RT. For work up the reaction mixture was mixed with 1N NaOH (10 ml) and stirred for 10 min. After phase separation the aqueous phase was extracted with dichloromethane (2×10 ml). The combined organic phases were dried with sodium sulphate, filtered and concentrated to low volume in a vacuum. 741 mg of light brown solid was obtained, which was separated by chromatography [silica gel 60 (80 g); ethyl acetate/methanol (15:1; 1.51); (10:1; 500 ml); 1:1; 500 ml)].

Provenance & Evidence