ChemicalBook CAS DataBase List Dextromethorphan

Dextromethorphan synthesis

10synthesis methods

Product Name:Dextromethorphan
CAS Number:125-71-3
Molecular formula:C18H25NO
Molecular Weight:271.4

Dextromethorphan, (9α,13α,14α)-3-methoxy-17-methylmorphinane (23.2.1), is synthesized from ()-3-hydroxy-N-methylmorphinane by methylating the phenol hydroxyl group using phenyltrimethylammonium chloride and sodium methoxide in methanol. The resulting racemic product ()-3-methoxy-N-methylmorphinane is separated into isomers using D-tartaric acid, which produces dextromethor-phan.

Dextromethorphan hydrobromide monohydrate

6700-34-1
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$28.00/50mg

125-71-3
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$18.00/1mg

Yield:125-71-3 97.98%

Reaction Conditions:

with sodium hydroxide in chloroform;water; for 0.5 h;

Steps:

Demethylation of DM

A solution of 2.68 g (67 mmol) of sodium hydroxide in 50 ml of water was added to a solution of 25 g (67 mmol) of dextromethorphan hydrobromide hydrate in 100 ml of chloroform.
The reaction mixture was stirred for 30 min on a magnetic stirrer.
The organic layer was separated and dried with anhydrous sodium sulfate.
The solvent was evaporated on a rotavap.
The obtained freebase of dextromethorphan was a dense and viscous off-white oil which solidified upon standing. Yield: 17.95 g (97.98%).

References:

Jozwiak, Krzysztof;Targowska-Duda, Katarzyna M.;Kaczor, Agnieszka A.;Kozak, Joanna;Ligeza, Agnieszka;Szacon, Elzbieta;Wrobel, Tomasz M.;Budzynska, Barbara;Biala, Grazyna;Fornal, Emilia;Poso, Antti;Wainer, Irving W.;Matosiuk, Dariusz [Bioorganic and Medicinal Chemistry,2014,vol. 22,# 24,p. 6846 - 6856]