The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Date of Patent:
May. 20, 1980

Filed:

Apr. 14, 1978
Applicant:
Inventors:

Robert F Parcell, Lakeland, FL (US);

Ivan C Nordin, Ann Arbor, MI (US);

Assignee:

Warner-Lambert Company, Morris Plains, NY (US);

Attorneys:
Primary Examiner:
Int. Cl.
CPC ...
C07D / ; C07D / ;
U.S. Cl.
CPC ...
2602 / ; 2602452 ;
Abstract

A process for the preparation of cis-(.+-.)-3,4-dihydro-N,N,2-trimethyl-2H-1-benzopyran-3-amine (I), a known antidepressant, is disclosed. The process of the invention is a multi-step process starting with 2-methyl-2H-1-benzopyran (II), which involves the production of novel intermediates (2.alpha.,3.beta.,4.alpha.)-(.+-.)-3,4-dihydro-2-methyl-4-(methylamino)-2H -1-benzopyran-3-ol (IV) and its hydrogen sulfate ester (V) as well as (1a.alpha.,2.beta.,7b.alpha.)-(.+-.)-1,1a,2,7b-tetrahydro-1,2-dimethyl[1]b enzopyrano[3,4-b]azirine (VI) and cis-(.+-.)-3,4-dihydro-N,2-dimethyl-2H-1-benzopyran-3-amine (VII). In the final step of the process, compound VII is methylated to form compound I.


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