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Feclemine (phenetamine) is a spasmolytic drug.
Sodamide is used to alkylate cyclohexylphenylacetonitrile 893-23-0(1) (also used for drofenine) with 2-chloro-N,N,N',N'-tetraethylpropane-1,3-diamine 492-54-4(HCl: 4465-65-3 to give (2). Some rearrangement is possible to give a mixture of regioisomers. Sodamide catalyzed cleavage of the nitrile group in a separate step then completes the synthesis of feclemine (3).
Precursor: Alcohol:
Synthesis
The chemical synthesis is discussed:
Sodamide is used to alkylate cyclohexylphenylacetonitrile 893-23-0(1) (also used for drofenine) with 2-chloro-N,N,N',N'-tetraethylpropane-1,3-diamine 492-54-4(HCl: 4465-65-3 to give (2). Some rearrangement is possible to give a mixture of regioisomers. Sodamide catalyzed cleavage of the nitrile group in a separate step then completes the synthesis of feclemine (3).
Precursor: Alcohol:
References
{{reflist Antispasmodics Diethylamino compounds Cyclohexyl compounds Phenyl compounds