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

✍ Scribed by Christian T. Goralski; James R. McCarthy; J. W. Linowski; R. A. Nyquist; C. L. Putzig

Publisher
John Wiley and Sons
Year
1981
Tongue
French
Weight
225 KB
Volume
18
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

N, N′ ‐Dimethyl 2‐naphthaleneethanimidamide monohydrochloride (DL‐588) is a potential psychotherapeutic agent for which a sample of carbon‐13 labelled material was required for metabolism studies. The sample of 90% ^13^C enriched DL‐588 was prepared starting with 90% ^13^C enriched potassium cyanide in three steps. 2‐(Bromomethyl)naphthalene was treated with the ^13^C potassium cyanide under phase transfer catalysis. The resulting ^13^C‐2‐napthylacetonitrile was converted to the imidate ester hydrochloride under Pinner reaction conditions (1). This intermediate was treated with excess methylamine in ethanol at 55° to give the title compound in an overall yield of 68%. The effects of ^13^C labelling on the ^1^H NMR spectra of the final product and intermediates are discussed.

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