1-[2-(3-Methoxyphenyl)cyclohexyl]-N,N-dimethylmethanamine → Phenol, 3-[2-[(dimethylamino)methyl]cyclohexyl]-

Participants

Reaction Steps

125 g (440 mmole) of the precursor 1-(2-(3-methoxyphenyl)cyclohexyl)-N,N-dimethylmethaneamine and 500 ml of hydrobromic acid (47%, in water) were introduced together into a single necked flask and stirred under reflux for 2 hours using a magnetic stirrer. After conclusion of the reaction, the hydrogen bromide was distilled off by applying a vacuum (water-jet pump). The distillation residue was added to 250 ml water, and the suspension was covered with a layer of 1000 ml ethyl acetate. The pH of the reaction mixture was adjusted to pH 8 with aqueous sodium-hydroxide solution (c=32% w/w), accompanied by cooling of the reaction mixture with ice. Organic and aqueous phases were separated, the aqueous phase was extracted three times with 350 ml portions of ethyl acetate. In the process, the pH value was monitored and maintained at a value of at least pH 8 using aqueous sodium-hydroxide solution (c=32% w/w). The mixture was extracted two more times with 150 ml portions of ethyl acetate, and the organic phase was dried with MgSO4. The solvent was removed in a rotary evaporator (bath temperature 44° C., vacuum <20 mbar). The yield of crude product 3-[2-(dimethylamino)methyl(cyclohex-1-yl)]phenol amounted to 101 g. The crude product 3-[2-(dimethylamino)methyl(cyclohex-1-yl)]phenol was added to 100 ml acetone and stirred until the light-brown material solidified. Subsequently the material was filtered out by suction and washed with a little diethyl ether. The yield amounted to 48%, relative to the quantity of crude product employed.

Provenance & Evidence