Hydrochloric Acid → HCID 21519232, compound

Participants

Reaction Steps

The procedure of Example II is followed except that 2-phenylcyclohexanone is replaced by 2-(p-Methoxyphenyl)cyclohexanone and piperidine is replaced by dimethylene. By this method is obtained 196 g crude Ethyl-2-(1-hydroxy-2-[p-methoxyphenyl]cyclohexyl) propionate from 128.7 g 2-(p-Methoxyphenyl)cyclohexanone (which is prepared by known methods) and 121.8 g Ethyl-2-bromopropionate; 50 g crude 2-(1-Hydroxy-2-[p-methoxyphenyl]cyclohexyl) propionic acid from 196 g Ethyl-2-(1-hydroxy-2-[p-methoxyphenyl]cyclohexyl)propionate; 54.6 g crude 2-(1-Hydroxy-2-[p-methoxyphenyl]cyclohexyl)propanol from 50 g 2-(1-Hydroxy-2-[p-methoxyphenyl]cyclohexyl)propionic acid. The crude 2-(1-Hydroxy-2-[p-methoxyphenyl]cyclohexyl)propanol is converted to the tosylate and treated with 125 ml dimethylamine (according to the procedure of Example II) to give 44 g crude base which is converted to the hydrochloride and recrystallized from isopropanol to give 33.5 g product, m. 245-6.

Provenance & Evidence