Dapoxetine

The Uses of Dapoxetine

Dapoxetine-d7 Hydrochloride is a Labelled Dapoxetine (D185700). A selective serotonin reuptake inhibitor (SSRI).

The Uses of Dapoxetine

Antidepressant.

Definition

ChEBI: Dapoxetine is a member of naphthalenes.

Clinical Use

Dapoxetine is a selective serotonin re-uptake inhibitor (SSRI) which has been approved in Finland and Sweden for the treatment of premature ejaculation.Dapoxetine was discovered and developed by Lilly and was licensed to Alza, a wholly-owned subsidiary of Johnson & Johnson.

Synthesis

Several synthetic routes for the preparation of dapoxetine have been disclosed, all on gram scale. Based on the routes and yields, the most likely process route is described in the scheme 4. Commercially available (R)-(+)-3-chloro-1-phenyl- 1-propanol (19) was reacted with 1-naphthol in the presence of 50% aqueous sodium hydroxide in DMF to give ether 20 in 90% yield. Activation of the secondary alcohol was accomplished through treatment of 20 with methane sulfonyl chloride and triethylamine with catalytic DMAP. Upon complete conversion to the corresponding mesylate, dimethylamine was added to the reaction mixture. The addition of hydrochloric acid in ethyl acetate to the resultant crude product gave dapoxetine hydrochloride (IV) in 67% yield. Purification of this material by re-crystallization from isopropanol provided IV in 86% yield and in 99.6% ee.