Acetic Anhydride → Pseudoephedrine Hydrochloride

HRID 1732428

Reaction equation

[CH3:1][C@H:2]([NH:11][CH3:12])[C@H:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[ClH:13].C(OC(=O)C)(=O)C>>[CH3:1][C@H:2]([NH:11][CH3:12])[C@@H:3]([OH:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[ClH:13]

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 65326Ephedrine Hydrochloride

Product 1

HCID 9581Pseudoephedrine Hydrochloride

Procedure

It has also been reported that the reaction of 1-ephedrine hydrochloride with 10 moles excess acetic anhydride gave d-pseudoephedrine hydrochloride. No yields were reported. Schmidt and Calliess, Arch. Pharm., 250, 154 (1912).

Sources & evidence

ORD record: ord-8016b3e9da5c4d3b97578994cfdd3b91
Source dataset: uspto-grants-1980_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04237304

Linked notes

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