Process for the preparation of cis-(.+-.)-3,4-dihydro-N,N,2-trim

Details Process for the preparation of cis-(.+-.)-3,4-dihydro-N,N,2-trim Process for the preparation of cis-(.+-.)-3,4-dihydro-N,N,2-trim

1978-04-14

1980-05-20

Chan, Nicky

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2602452, C07D23002, C07D31104

Patent

active

042038952

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.

REFERENCES:
patent: 3607886 (1971-09-01), Lockhart
patent: 3880834 (1975-04-01), Kotera et al.
patent: 3890302 (1975-06-01), Kotera et al.
patent: 4048317 (1977-09-01), Watts

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