Ammonium Chloride → HCID 131723350, compound

Participants

Reaction Steps

0.22 g (9.0 mmole) of magnesium turnings was stirred in 5 ml of ether of analysis purity. 2.03 g (9.0 mmole) of 4-bromo-benzotrifluoride dissolved in 5 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. 2.00 g (7.5 mmole) of the 2-[(4-chloro-phenyl)dimethylaminomethyl]cyclohexanone prepared according to Example 58 were dissolved in 10 ml of ether, added dropwise to the Grignard reagent while cooling in an ice bath, and stirred for 15 hours at RT. The reaction mixture was worked up by adding 10 ml of saturated ammonium chloride solution while cooling in an ice bath, and was extracted three times at RT with 15 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). 2.65 g of crude base (85.4% of theory) were obtained, from which a hydrochloride was precipitated according to Example 1 (3rd stage) with chlorotrimethylsilane/water in 2-butanone. The base was freed from the hydrochloride with 20 ml of water and 5 ml of ammonia solution (25 vol. %), extracted three times with 20 ml of ether each time, and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated by evaporation on a rotary evaporator (500 to 10 mbar). 0.50 g of crude base (16.2% of theory) was obtained, from which 0.20 g of 2-[(4-chlorophenyl)dimethylaminomethyl]-(4-trifluoromethylphenyl)cyclohexanol, hydrochloride (6.0% of theory) with a melting point above 240° C. was obtained according to the procedure described in Example 1 (3rd Stage) with chlorotrimethylsilane/water in 2-butanone.

Provenance & Evidence