The synthesis of 13C labelled N, N′-dimethyl 2-naphthaleneethanimidamide monohydrochloride, a potential psychotherapeutic agent

Autor: J. W. Linowski, James R. McCarthy, C. L. Putzig, Christian T. Goralski, Richard A. Nyquist
Rok vydání: 1981
Předmět:
Zdroj: Journal of Labelled Compounds and Radiopharmaceuticals. 18:1047-1053
ISSN: 0362-4803
DOI: 10.1002/jlcr.2580180716
Popis: N, N'-Dimethyl 1-chloro-2-naphthaleneethanimidamide monohydrochloride is a potential psychotherapeutic agent for which a sample of carbon-13 labelled material was required for metabolism studies. A sample of 90% enriched N, N'-dimethyl 1-chloro-2-naphthaleneethanimidamide monohydrochloride was prepared from 90% carbon-13 enriched potassium cyanide and 2-methylnaphthalene in five steps. Chlorination of 2-methylnaphthalene with sulfuryl chloride gave 1-chloro-2-methylnaphthalene in 69% yield. Bromination of 1-chloro-2-methylnaphthalene with N-bromosuccinimide in carbon tetrachloride in the presence of catalytic benzoyl peroxide afforded 2-(bromomethyl)-1-chloronaphthalene in 59% yield. Treatment of 2-(bromomethyl)-1-chloronaphthalene with potassium cyanide in aqueous ethanol afforded 13C-1-chloro-2-naphthylacetonitrile in 89% yield. The nitrile was converted to the imidate ester hydrochloride in 89% yield under Pinner reaction conditions (1). This intermediate was treated with excess methylamine in ethanol at 40-55°C to give the title compound in an overall yield of 27% from 2-methylnaphthalene. The effects of the 13C labelling on the infrared and 1H and 13C NMR spectra of the intermediates and the final product are discussed.
Databáze: OpenAIRE
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