Hydrochloric Acid → HCID 18753166, compound

Participants

Reaction Conditions

Reaction Steps

3 g of the Z-3-[4-Dimethylaminomethyl-3-(3-hydroxy-phenyl)-cyclohex-2-enylidenmethyl]-benzoic acid methyl ester, as the base, prepared according to example 32 were dissolved in 30 ml methanol, and 30 ml 1 N potassium hydroxide solution were added. The mixture was stirred at 60° C. for 2 hours. After the reaction mixture had cooled to room temperature, 1 N hydrochloric acid was added to the mixture until a pH of 4 was established. The phases were separated and the aqueous phase was washed 3 times with 20 ml ethyl acetate each time. The combined organic phases were dried over magnesium sulfate and freed from the solvent in vacuo. Z-3-[4-Dimethylaminomethyl-3-(3-hydroxy-phenyl)-cyclohex-2-enylidenmethyl]-benzoic acid, 2.7 g in the form of an orange-yellow oil, was obtained in this way. To prepare the hydrochloride, the base was dissolved in 10 ml acetone, and an equimolar amount of trimethylchlorosilane and water was added. 2.4 g (77.7% of theory) Z-3-[4-dimethylaminomethyl-3-(3-hydroxy-phenyl)-cyclohex-2-enylidenmethyl]-benzoic acid hydrochloride were obtained in this way.

Provenance & Evidence