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Title:
IMINE SALT DERIVATIVE AND PREPARATION METHOD THEREFOR, AND PREPARATION METHOD FOR NICOTINE
Document Type and Number:
WIPO Patent Application WO/2021/056811
Kind Code:
A1
Abstract:
Disclosed are an imine salt derivative and a preparation method therefor, and a preparation method for nicotine. The preparation method for nicotine comprises the following steps: adding an imine salt derivative having a general formula of (I) or (II) and a reducing agent into a solvent and allowing reaction to occur to obtain a solution of racemic nicotine; adding a second quenching agent into the solution of racemic nicotine to obtain a solution of a nicotine precursor; and adding an extractant into the solution of a nicotine precursor, performing vacuum concentration, and removing the solvent by drying to obtain nicotine. In the present invention, racemic nicotine is obtained by reducing an imine salt derivative intermediate, which is synthesized for the first time, using an inexpensive reducing agent under relatively mild conditions. Compared with existing nicotine synthesis processes, the method of the present invention has the advantages of having mild synthesis process conditions, simple equipment requirements, and high product purity and synthesis rates, and is particularly suitable for industrial production.

Inventors:
OU JUN (CN)
HAN KUIYUAN (CN)
Application Number:
PCT/CN2019/121980
Publication Date:
April 01, 2021
Filing Date:
November 29, 2019
Export Citation:
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Assignee:
SHENZHEN HELGETECH CO LTD (CN)
International Classes:
C07D401/04; C07C51/41; C07C63/08; C07C303/32; C07C309/19
Foreign References:
CN102617547A2012-08-01
Other References:
KOVACIC, PETER ET AL.: "Reduction potentials of imine-substituted, biologically active pyridines:possible relation to activity", FREE RADICAL RESEARCH COMMUNICATIONS, vol. 10, no. 3, 31 December 1990 (1990-12-31), ISSN: 8755-0199
IDE, AKIO ET AL.: "Synthesis of 3-(1-methyl-2-pyrrolidinyl) quinoline", JOURNAL OF THE CHEMICAL SOCIETY OF JAPAN, vol. 91, no. 6, 31 December 1970 (1970-12-31)
WAGNER, F.F. COMINS, D.L.: "Recent advances in the synthesis of nicotine and its derivatives", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, AMSTERDAM, NL, vol. 63, no. 34, 12 July 2007 (2007-07-12), AMSTERDAM, NL, pages 8065 - 8082, XP022149763, ISSN: 0040-4020, DOI: 10.1016/j.tet.2007.04.100
WU YAXIAN, WANG XIAO-YU, HE LI-QIN: "Synthesis of Nicomethanol Nicotinate", ANHUI CHEMICAL INDUSTRY, vol. 39, no. 4, 1 August 2013 (2013-08-01), pages 34 - 38, XP055796147, DOI: 10.3969/j.issn.1008-553X.2013.04.011
GÄRTNER PETER, BICA KATHARINA, EINZINGER CHRISTIAN: "Synthesis of Partially Deuterated N -Nitrosamines ? New Standards in Tobacco-smoke Analysis", MONATSHEFTE FÜR CHEMIE / CHEMICAL MONTHLY, SPRINGER VIENNA, VIENNA, vol. 135, no. 5, 1 May 2004 (2004-05-01), Vienna, pages 549 - 555, XP055795773, ISSN: 0026-9247, DOI: 10.1007/s00706-003-0152-8
Attorney, Agent or Firm:
SHENZHEN INNOVATION INTELLECTUAL PROPERTY AGENCY CO., LTD (CN)
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