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Synthesis 2020; 52(22): 3374-3377
DOI: 10.1055/s-0040-1707353
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© Georg Thieme Verlag Stuttgart · New York

A Catalyst-Free, Temperature-Driven One-Pot Synthesis of 1-Adamantylhydrazine Hydrochloride

Anjana Delpe Acharige
,
Raul Neri
,
James Hodgson
,
Stefan H. Bossmann  ∗
Department of Chemistry, Kansas State University, CBC Building 201, Manhattan, KS, 66506-0401, USA   Email: sbossman@ksu.edu
› Author AffiliationsThe work was supported by the National Institutes of Health (NIH) (NIH/DHHS 1R01Al121364-01A1).
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Publication History

Received: 30 June 2020

Accepted after revision: 23 July 2020

Publication Date:
25 August 2020 (online)

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Abstract

1-Adamantylhydrazine can be a versatile intermediate for many biologically active compounds as adamantyl possesses a wide spectrum of medicinal properties. Described here is a detailed one-pot synthesis of 1-adamantylhydrazine, carried out on a milligram to gram scale, that steadily delivers a highly stable product used to carry out the synthesis of 1-(adamantan-1-yl)-1H-pyrazol-3-amine for bacterial studies. The reaction employs inexpensive, catalyst free, readily available starting materials. In the synthesis of 1-(adamantan-1-yl)-1H-pyrazol-3-amine, the use of a continuous extraction method allows for complete extraction of the target product into the organic layer and increases the overall percentage yield.

Key words

SN1 substitution - hydrazines - adamantane - 1H-pyrazol-3-amine - continuous extraction

Supporting Information

    Supporting Information for this article is available online at https://doi.org/10.1055/s-0040-1707353.
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