Process for recycling amine isomer

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

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564307, 564308, 564425, 564428, C07C20988

Patent

active

050829700

ABSTRACT:
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 contacting 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 mixture achieves a constant value of about 2:1 on a weight-by-weight basis. The aforesaid resultant mixture is useful as an intermediate 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.

REFERENCES:
patent: 3506714 (1970-04-01), Hinkley et al.
patent: 4463176 (1984-07-01), Dennis et al.
patent: 4536518 (1985-08-01), Welch, Jr. et al.
patent: 4556676 (1985-12-01), Welch, Jr. et al.

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