Acetic Anhydride → HCID 10277295, compound

Participants

Reaction Steps

N′-[2-(1H-indol-3-yl)ethyl]-N,N-dimethyl-1-pyridin-2-yl cyclohexane-1,4-diamine (250 mg) was dissolved in dry pyridine (5 ml), acetic anhydride (0.64 ml) was added and the mixture was stirred for 22 hours at room temperature. Some ice was added to the reaction mixture and it was then concentrated to low volume. The residue was taken up in 1M sodium hydroxide solution (20 ml) and ethyl acetate (20 ml) and stirred. A white solid was left behind, which could be suction filtered (86 mg). The aqueous phase of the filtrate was extracted with ethyl acetate (2×20 ml). The combined organic extracts were concentrated to low volume after drying. The residue obtained in this way was identical to the solid obtained earlier. Both substances were combined. 219 mg N-(4-dimethylamino-4-pyridin-2-yl cyclohexyl)-N-[2-(1H-indol-3-yl)ethyl] acetamide were obtained (mp 209–210° C.), of which 195 mg were dissolved in 2-butanone (25 ml) with gentle heating to 40° C. and converted into the corresponding dihydrochloride with chlorotrimethyl silane (0.303 ml) (white solid; 219 mg; mp 244–247° C.).

Provenance & Evidence