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Some acid catalised rearrangements of Anhydrocryptopine

✍ Scribed by D.W. Brown; S.F. Dyke

Publisher
Elsevier Science
Year
1966
Tongue
French
Weight
263 KB
Volume
7
Category
Article
ISSN
0040-4039

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✦ Synopsis

When the opium alkaloid cryptopine (1) is treated' with phosphorus oxychloride, ring-closure occurs to yield (2), which is transformed by potassium hydroxide into anhydrocryptopine (3), C21H2LN04.

In the course of Perkin's classical studies'on cryptopine he described the reactions of anhydrocryptopine with boihconcentrated and dilute hydrochloric acids.

Prompted by our interest in the chemistry of L,2-dihydroiscquinoLines2 we decided to re-investigate these reactions.

After boiling anhydrocryptopine (3) with cont. HCl for 45 seconds.

Berkin isolated three bases, which he named epicryptopines A, B and C, C21H23N05r and for which he proposed the structures (4), ( 5). and ( 6),

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