(S)-3-[1-(Dimethylamino)ethyl]phenol hydrochloride
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Chemical Product Description & Applications
(S)-3-[1-(Dimethylamino)ethyl]phenol hydrochloride is a chiral phenolic intermediate used in rivastigmine synthesis. It supplies the S-configured dimethylaminoethyl substituent and a phenolic oxygen for carbamate formation. Reaction at that oxygen introduces the N-ethyl-N-methylcarbamoyl group while retaining the stereocenter in the side chain.
The selected material is the hydrochloride salt rather than the free phenol or its opposite enantiomer. The tertiary amine is protonated in the isolated salt, whereas the phenolic group provides the functionalization site needed downstream. This combination permits a defined chiral fragment to be handled as a salt before conversion into the carbamate structure of rivastigmine and, subsequently, the required final drug-substance form.
Typical Applications
- Rivastigmine carbamate synthesis: Used as the chiral phenol precursor in O-carbamoylation routes that install the ethylmethylcarbamate group and construct the rivastigmine molecular structure.
- Chiral intermediate isolation in process routes: Used as an isolable hydrochloride in rivastigmine manufacturing-route development, separating recovery of the S-configured phenol from the subsequent phenolic functionalization stage.
Specifications
| Parameter | Specification | Test Method |
|---|---|---|
| Appearance | Solid; color consistent with the reference sample | Visual inspection |
| Identification | Consistent with authenticated reference | FTIR fingerprint comparison |
| Chromatographic purity | ≥98.0 area% | HPLC with suitable UV or CAD detection |
| Total organic impurities | ≤2.0 area% | HPLC, area normalization |
| Largest individual impurity | ≤1.0 area% | HPLC, area normalization |
| Water | ≤1.0% w/w | Karl Fischer titration |
| Stereochemical purity | ≥98.0 area% specified stereoisomer | Chiral HPLC or stereoisomer-resolving GC |
Specifications describe the standard grade. Tolerance, test method and documentation package are confirmed per order.
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