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Process for the preparation of (1S-cis)-4-(3,4 dichlorophenyl)-1,2,3,4-tetrahydro- N-methyl-1-naphthalenamine hydrochloride

IP.com Disclosure Number: IPCOM000180806D
Publication Date: 2009-Mar-17
Document File: 2 page(s) / 11K

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The IP.com Prior Art Database

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     Process for the preparation of (1S-cis)-4-(3,4 dichlorophenyl)-1,2,3,4-tetrahydro- N-methyl-1-naphthalenamine hydrochloride
(1S-cis)-4-(3,4 dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine hydrochloride is known as SRT·HCl. SRT·HCl having the following chemical structure:

NHCH3

Cl

Cl

    SRT·HCl is approved, under the trademark Zoloft®, by the U.S. Food and Drug Administration, as a serotonin re-uptake inhibitor, used for the treatment of depression, obsessive-compulsive disorder, panic disorder and post-traumatic disorder. Only cis SRT·HCl is therapeutically active.

    Described is a process for preparing SRT·HCl by a process comprising: dissolving HCl in n-butanol; adding n-heptane or hexane; heating; adding a solution of (1S-cis)-4-(3,4 dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine base ("SRT base") or (1S- cis)-4-(3,4 dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine mandalate ("SRT mandalate") in n-butanol; and recovering.

     Preferably, the dissolution of HCl in n-butanol is at a temperature of about 0oC to about 45 oC. Preferably, the heating is to a temperature of about 45oC to about 60oC. SRT base and SRT mandalate may be prepared by any method known in the art, for example, by the process described in US patent no. 4,536,518 and in US patent no. 5,248,699 respectively. The addition of the solution of SRT base or SRT mandalate in n-butanol is done slowly. The recovery comprises...