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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2378503Generated: October 31, 2026

Benzoate → Cyclohexanol, 2-((dimethylamino)methyl)-1-(3-methoxyphenyl)-, hydrochloride (1:1)

https://huagongshe.com/reaction/2378503

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBenzoateHCID 242—
Reactant2-((Dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexanolHCID 5523—
ReactantSodium HydroxideHCID 14798—
ReactantIsopropanol hydrochlorideHCID 21912024—
ReactantHCID 178489946HCID 178489946—
SolventWaterHCID 962—
SolventIsopropanolHCID 3776—
ProductCyclohexanol, 2-((dimethylamino)methyl)-1-(3-methoxyphenyl)-, hydrochloride (1:1)HCID 9971980—

Reaction Conditions

Temperature75 °C

Reaction Steps

In a reaction flask 160 g tramadol salicylate (or benzoate) salt was stirred with about 800 ml water and pH was adjusted to 11-12 by 30% aqueous NaOH solution. The tramadol free base was extracted with toluene, washed with water, and toluene was evaporated under reduced pressure. The oil obtained (about 100 gm) was dissolved in 300 ml isopropyl alcohol. In a separate flask HCI gas was passed in isopropyl alcohol. This isopropyl alcohol-HCI solution was added to tramadol base solution in isopropyl alcohol at about 30° C. till the pH attained 3-4. The mixture was stirred, heated to about 75° C., and then cooled to 0-5° C. The precipitated product was filtered, washed with chilled isopropyl alcohol and dried to obtain 92 gm Tramadol hydrochloride (cis=99.95% & trans=0.05%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07470816B2
Source datasetuspto-grants-2008_12
ORD IDord-2e406fb06f2b49d1b7575553e6630f2a
Source noteuspto-grants-2008_12