Ammonium Chloride → 2-(Dimethylaminophenyl-methyl)-1-(2-methylsulfanylphenyl)cyclohexanol, hydrochloride

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Reaction Conditions

Reaction Steps

0.811 g (3.24 mmole) of 2-methylmercaptoiodobenzene were dissolved in 2 ml of ether, cooled to −10° C., and 1.62 ml (3.24 mmole) of isopropylmagnesium chloride (2 M solution in tetrahydrofuran) were added dropwise. After stirring for one hour at ° C., 0.50 g (2.16 mmole) of the 2-(dimethylaminophenylmethyl)cyclohexanone prepared according to Example 1 and dissolved in 2 ml of ether was added dropwise, and the whole was stirred for 15 hours at RT. The reaction mixture was worked up by adding 2 ml of saturated ammonium chloride solution while cooling in an ice bath and was extracted three times at RT with 5 ml of ether each time. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated by evaporation on a rotary evaporator (500 to 10 mbar). 0.84 g of crude base (109% of theory) was obtained, from which 0.483 g of 2-(dimethylaminophenyl-methyl)-1-(2-methylsulfanylphenyl)cyclohexanol, hydrochloride (38.0% of theory) was obtained according to the procedure described in Example 1 (3rd Stage) with chlorotrimethylsilane/water in 2-butanone. The hydrochloride decomposes on heating above 230° C.

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