Process for recycling amine isomer

Details Process for recycling amine isomer Process for recycling amine isomer

C - Chemistry, Metallurgy

07

C

C07C 211/42 (2006.01) C07C 209/68 (2006.01) C07C 211/38 (2006.01)

Patent

CA 2105393

A novel process for converting trans-isomeric N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine to cis-isomeric N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine is disclosed. The process involves contact- ing trans-isomeric N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine, or a mixture of same with up to about an equal part by weight of the corresponding cis-isomer, with a basic equilibration agent like potassium tert.-butoxide in a reaction-inert polar organic solvent to ultimately afford a cis/trans-mixture wherein the amount of cis-amine present in said mix- ture achieves a constant value of about 2:1 on a weight-by-weight basis. The aforesaid resultant mixture is useful as an intermedi- ate product that ultimately leads to pure cis-(1S)(4S)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine (sertraline), which is a known antidepressant agent.

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