Chloride → HCID 22447911, compound

Participants

Reaction Conditions

Reaction Steps

0.38 g (15.6 mmole) of magnesium turnings was stirred in 15 ml of tetrahydrofuran of analysis purity. 3.39 g (15.6 mmole) of 1-bromo-2,5-dimethoxybenzene dissolved in 15 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 1.5 hours at 65° C. 3.0 g (13.0 mmole) of the 2-(dimethylaminophenylmethyl) cyclohexanone prepared according to Example 1 were dissolved in 15 ml of tetrahydro-furan, 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 anmonium chloride solution while cooling in an ice bath, and was extracted three times at RT with in each case 60 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). 5.17 g of crude base (108% of theory) were obtained. 4.43 g of 1-(2,5-dimethoxy-phenyl)-2-(dimethylaminophenylmethyl)cyclohexanol, hydrochloride (84.2% of theory) with a melting point above 240° C. were obtained from the crude base according to the procedure described in Example 1 (3rd stage) with chlorotri-methylsilane/water in 2-butanone.

Provenance & Evidence