Hydrochloric Acid → HCID 9863763, compound

Participants

Reaction Conditions

Reaction Steps

0.38 g (15.5 mmole) of magnesium turnings was stirred in 5 ml of tetrahydrofuran of analysis purity. 3.81 g (15.5 mmole) of 1-(4-bromophenoxy)-1-ethoxyethane dissolved in 5 ml of tetrahydrofuran 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 55° C. 3.0 g (13.0 mmole) of the 2-(dimethylaminophenylmethyl)cyclohexanone prepared according to Example 1 were dissolved in 15 ml of tetrahydrofuran, 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 30 ml of saturated ammonium chloride solution while cooling in an ice bath, and was extracted three times at RT, each time with 80 ml of ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated on a rotary evaporator (500 to 10 mbar). 5.25 g of crude base were obtained, which were dissolved in 20 ml of ether followed by the addition of 10 ml of hydrochloric acid (1 N). The aqueous phase was separated and sufficient sodium bicarbonate was added to adjust the pH to ca. 8.The base was extracted three times, each time with 20 ml of ether, and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated by evaporation on a rotary evaporator (500 to 10 mbar). 1.96 g of crude base (46.3% of theory) were obtained, from which 1.8 g of 4-[2-(dimethylaminophenylmethyl)-1-hydroxycyclohexyl]phenol, hydrochloride were obtained (38.6% of theory) with 0.49 ml of hydrochloric acid (32 m %,) and 20 ml of acetone. The hydrochloride decomposes on heating above 140° C.

Provenance & Evidence