Ammonia → HCID 131723352, compound

Participants

Reaction Steps

0.34 g (14.0 mmole) of magnesium turnings was stirred in 10 ml of ether of analysis purity. 3.16 g (14.0 mmole) of 4-bromobenzotrifluoride 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. The base was freed from 3.5 g (12.0 mmole) of the hydrochloride of 4-[dimethylamino-(2-oxocyclohexyl)methyl]benzonitrile obtained according to stage 1 with 30 ml of water and 5 ml of ammonia solution (25 vol. %), extracted three times with 30 ml of ether each time, and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated by evaporation on a rotary evaporator without heating (500 to 10 mbar). 3.0 g (11.7 mmole) of this base 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 20 ml of saturated ammonium chloride solution while cooling in an ice bath, and was extracted three times at RT with 20 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). 3.52 g of crude base (74.7% of theory) were obtained, from which 0.17 g of 4-{dimethylamino-[2-hydroxy-2-(4-trifluoromethylphenyl)cyclohexyl]methyl}-benzonitrile, hydrochloride (3.3% of theory) having a melting point above 250° C. was obtained according to the procedure described in Example 1 (3rd Stage) with chlorotrimethylsilane/water in 2-butanone.

Provenance & Evidence