Ammonium Chloride → HCID 131723332, compound

Participants

Reaction Conditions

Reaction Steps

2.61 g (13.0 mmole) of 4-bromo-1,2-methylenedioxybenzene were dissolved in 10 ml of tetrahydrofuran and cooled to −70° C. under nitrogen in a dry ice/isopropanol bath. 7.9 ml (13.0 mmole) of n-butyllithium (1.6 M in hexane) were added dropwise while stirring so that the temperature did not rise above −60° C. The reaction mixture was stirred for a further 30 minutes and then 3.0 g (10.8 mmole) of the 2-[dimethylamino-(3-methoxyphenyl)methyl]cyclohexanone prepared according to Example 9 and dissolved in 10 ml of tetrahydrofuran were added dropwise while cooling in an ice bath, and the whole was heated to RT within two hours. The reaction mixture was worked up by adding 20 ml of saturated ammonium chloride solution while cooling in an ice bath, and was extracted three times at RT, each time with 20 ml of ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated by evaporation on a rotary evaporator (500 to 10 mbar). 4.10 g of crude base (98.8% of theory) were obtained, from which 1.96 g of 1-benzo[1,3]dioxol-5-yl-2-[dimethylamino-(3-methoxyphenyl)methyl]cyclohexanol, hydrochloride (43.2% of theory) were obtained according to the procedure described in Example 1 (3rd stage) with chlorotrimethylsilane/water in 2-butanone. The hydrochloride decomposes on heating above 109° C.

Provenance & Evidence