Sodium Hydroxide → 2-((Dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexanol

Participants

Reaction Steps

60 g of (+/−)-Tramadol hydrochloride (0.0228 mol) were suspended in 96 ml of water and treated with 32 g of crushed ice. To this suspension was added 26 ml of 36% sodium hydroxide solution. The mixture was then extracted with dichloromethane 140 ml, followed by re-extraction with a further 40 ml of dichloromethane. The organic layers were combined and dried over magnesium sulphate. The solvent was then removed under vacuum to give the (+/−)-Tramadol free base quantitatively as a yellow oil. This was taken up in 48 ml of ethanol and added to a solution of 30 g (L)-(−)-tartaric acid (0.0228 mol) in 224 ml of ethanol. This solution was stirred at 20° C. for two hours, and then allowed to stand for 24 hours at 4° C.

Provenance & Evidence