Ammonia → HCID 131723353, compound

Participants

Reaction Steps

The base was freed from 3.0g (10.6 mmole) of the hydrochloride of 2-(dimethylamino-o-tolylmethyl) cyclohexanone 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). 2.50 g (10.2 mmole) of this base were dissolved in 15 ml of tetrahydrofuran, added dropwise while cooling in an ice bath to 6.1 ml (12.2 mmole) of phenylmagnesium chloride (2 M solution in tetrahydro-furan), and stirred for 15 hours at RT. The reaction mixture was worked up by adding 15 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). 3.12 g of crude base (94.5% of theory) were obtained, from which 1.97 g of 2-(dimethylamino-o-tolylmethyl)-1-phenylcyclohexanol, hydrochloride (53.7% 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 137° C.

Provenance & Evidence