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Issue 0, 1971
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Phenothiazynes: preparation of 2- and 3-tertiary aminophenothiazines


A possible general route to 2- and 3-tertiary aminophenothiazines is described.

The reaction of 1-chloro-(3) or 2-chloro-10-methylphenothiazine (4) with sodium or lithium derivatives of secondary amines affords the same 2-tertiary amino-10-methylphenothiazine, presumably via a phenothiazyne intermediate (11). Similarly, 3-chloro-(5) or 4-chloro-10-methylphenothiazine (6) gives the same tertiary amino-10-methylphenothiazine, presumably the 3-isomer, via a different phenothiazyne (32). Demethylation of 2- and 3-tertiary amino-10-methylphenothiazines with pyridine hydrochloride at 200° affords 2- and 3-tertiary aminophenothiazines in good yield. Reaction of 2-tertiary aminophenothiazines with sodamide–3-dimethyl-aminopropyl chloride in boiling toluene gave the 10-(3-dimethylaminopropyl) derivatives.

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J. Chem. Soc. C, 1971, 132-137
Article type

Phenothiazynes: preparation of 2- and 3-tertiary aminophenothiazines

D. H. Jones, J. Chem. Soc. C, 1971, 132
DOI: 10.1039/J39710000132

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