A practical synthesis of 1,3,4,14b‐tetrahydro‐2‐methyl‐10 H ‐pyrazino‐[1,2‐ a ]pyrrolo[2,1‐ c ][1,4]benzodiazepine (1:1) maleate | Zendy

Boyer S. K. | Zendy; Fitchett G. | Zendy; Wasley J. W. F. | Zendy; Zaunius G. | Zendy

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A practical synthesis of 1,3,4,14b‐tetrahydro‐2‐methyl‐10 H ‐pyrazino‐[1,2‐ a ]pyrrolo[2,1‐ c ][1,4]benzodiazepine (1:1) maleate

Author(s) -

Boyer S. K.,

Fitchett G.,

Wasley J. W. F.,

Zaunius G.

Publication year - 1984

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570210338

Subject(s) - chemistry , benzodiazepine , stereochemistry , tricyclic , hemiacetal , yield (engineering) , d 1 , biochemistry , materials science , receptor , metallurgy

A practical synthesis of the anti‐depressant, 1,3,4,14b‐tetrahydro‐2‐methyl‐10 H ‐pyrazino[1,2‐ a ]pyrrolo‐[2,1‐ c ][1,4]benzodiazepine (1:1) maleate (Aptazapine 10 ) is reported in seven steps and approximately 20% overall yield. The key step of the synthesis was the formation of the tricyclic intermediate methyl 10,11‐dihydro‐5 H ‐pyrrolo[2,1‐ c ][1,4]benzodiazepine‐11‐carboxylate (7) via a “Pictet‐Spengler” type condensation of o ‐aminobenzylpyrrole ( 6 ) and methyl glyoxylate or the methoxy hemiacetal thereof.

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