Ammonium Chloride → HCID 131723331, compound

Participants

Reaction Steps

0.29 g (12.0 mmole) of magnesium turnings was stirred in 5 ml of ether of analysis purity. 2.42 g (12.0 mmole) of 3-methoxybenzyl bromide dissolved in 10 ml of ether were added dropwise so that the reaction mixture boiled gently. After completion of the addition the reaction mixture was stirred for a further hour at RT. 3.0 g (10.0 mmole) of the 2-[dimethyl-amino-(4-trifluoromethylphenyl)methyl]cyclohexanone prepared according to stage 2 were dissolved in 5 ml of ether, added dropwise to the Grignard reagent while cooling in an ice bath, and stirred for 15 hours at RT. The reaction solution was worked up by adding 30 ml of saturated ammonium chloride solution while cooling in an ice bath, and was extracted three times at RT, each time with 50 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). 5.60 g of crude base (133% of theory) were obtained. 3.26 g of 2-[dimethylamino-(4-trifluoromethyl-phenyl)methyl]-1-(3-methoxybenzyl)cyclohexanol, hydrochloride (70.9% of theory) were obtained from the crude base according to the procedure described in Example 1 (3rd stage) with chlorotrimethylsilane/water in 2-butanone. The hydrochloride decomposes on heating above 133° C.

Provenance & Evidence