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13th October

13th October

A Scalable Synthesis of the Antidepressant Agomelatine by a Tandem Allylic Chlorination–Isomerization Process

Christos I. StathakisEfstratios Neokosmidis and Theocharis V. Koftis

Eur. J. Org. Chem. 2014, 6376–6379

A concise, scalable, and industrially applicable process for the synthesis of the antidepressant agomelatine is described. The process relies on a tandem allylic chlorination–isomerization sequence, on a tetralone-derived allyl carbinol 2, as the key transformation. The target compound is obtained in five steps from commercially available 7-methoxy-1-tetralone 1, in 52.3 % overall yield after final recrystallization.

Literature october '14

Figure 1. The synthetic route to the synthesis of agomelatine purified by recrystallisation

The synthesis is among the most efficient in terms of overall yield and cost effectiveness and is well suited for large industrial production. The experimental conditions are mild and envi- ronmentally friendly. In addition, common and easily accessible chemicals are involved, while the most expensive of those, namely DDQ, was used only in catalytic amounts. Efforts for further optimization of the synthetic process are currently underway.