| | 175591-09-0 Basic information More.. |
| Product Name: | Tapentadol Hydrochloride | | Synonyms: | 3-[(1R,2R)-3-(Dimethylamino)-1-ethyl-2-methylpropyl]phenol Hydrochloride;Tapentadol Hydrochloride;Tapentadol hcl;Phenol, 3-[(1R,2R)-3-(diMethylaMino)-1-ethyl-2-Methylpropyl]-, (HCl salt);3-[(1R,2R)-3-(DiMethylaMino)-1-ethyl-2-Methylpro;3-((2R,3R)-1-(diMethylaMino)-2-Methylpentan-3-yl)phenol hydrochloride;Phenol,3-[(1R,2R)-3-(diMethylaMino)-1-ethyl-2-Methylpropyl]-, hydrochloride (1:1);Tapentadol hydrochloride solution | | CAS: | 175591-09-0 | | MF: | C14H24ClNO | | MW: | 257.81 | | EINECS: | 687-970-4 | | Mol File: | 175591-09-0.mol |  |
Use
The synthesis of tapentadol hydrochloride begins with diethyl ketone, which is subjected to a standard Mannich condition to provide a b-dimethylamino intermediate. A Grignard reaction with 3-bromoanisole was followed by the separation of diastereomers and racemic resolution. Treatment with thionyl chloride converts the hydroxy group to its corresponding chloride, which is removed by treatment with zinc borohydride (generated from zinc chloride and sodium borohydride), with overall retention of stereochemistry. The methyl ether is cleaved in refluxing HBr to afford the tapentadol salt that is ultimately converted to the hydrochloride for formulation into 50-, 75-, and 100-mg immediate-release (IR) oral tablets.
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175591-09-0
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