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A kind of preparation method of six-membered bicyclic guanidine based on guanidine hydrochloride

A technology of six-membered bicyclic guanidine and guanidine hydrochloride, applied in directions such as organic chemistry, can solve problems such as unreported MTBD, and achieve the effects of low price, high yield and less environmental pollution

Active Publication Date: 2015-08-12
RAFFLES PHAMRMATECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is no mature process method for the synthesis of MTBD reported in the literature at present

Method used

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  • A kind of preparation method of six-membered bicyclic guanidine based on guanidine hydrochloride
  • A kind of preparation method of six-membered bicyclic guanidine based on guanidine hydrochloride
  • A kind of preparation method of six-membered bicyclic guanidine based on guanidine hydrochloride

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Experimental program
Comparison scheme
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Embodiment 1

[0021] Example 1: The synthesis equation is as follows.

[0022]

[0023] Step 1: Synthesis of TBD from Guanidine Hydrochloride:

[0024] Guanidine hydrochloride (95 g, 1 mol, 1 eq), 3,3-diaminodipropylamine (131 g, 1 mol, 1 eq) were added to the flask. Heat to 120°C to initiate the reaction, and continue to heat up to 150°C for 8 hours after initiation. Cool down to 70°C, add 300ml methanol, stir to dissolve. Then add 200ml of methanol solution of 1mol sodium methoxide to concentrate most of the methanol, add 300ml of dichloromethane, filter, and recrystallize the filter cake in 300ml of tetrahydrofuran, filter, wash the residue with 100ml of THF, and dry to obtain about 120g of TBD. The rate is 86%.

[0025] Step 2: Synthesis of MTBD from TBD:

[0026] Add TBD (50g, 1eq), potassium hydroxide (24g, 1.2eq) and 250ml of tetrahydrofuran to the bottle successively. Dimethyl sulfate (45.26g, 1eq) was added dropwise at room temperature. After dripping, react overnight at r...

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Abstract

The invention discloses a preparation method of hexahydric dicycloguanidine based on guanidine hydrochloride. The preparation method of the hexahydric dicycloguanidine comprises the following steps of: (1), synthesizing TBD (Chloropropyl Methyl Dichlorosilane) by utilizing guanidine hydrochloridel; (2), synthesizing hexahydric dicycloguanidine by utilizing TBD methylation. The preparation method disclosed by the invention is less in synthesis steps, simple and easy to implement, free of severe reaction conditions, capable of adopting a crystallization-distillation purifying method and easy to realize industrial production. The using reagents are low-toxic or non-toxic, and the environment pollution is less. The yields of the two steps are more than 85% and the yields are high. The used materials and reagents are cheap, so that the cost is low.

Description

technical field [0001] The invention relates to the field of organic compound synthesis, in particular to a method for preparing a six-membered bicyclic guanidine. Background technique [0002] Arginine exists in the active site of many enzymes and its guanidine side chain, usually in the form of protonated guanidinium ion, which can form double hydrogen bonds with biomolecules containing phosphate, nucleotide, and carboxylate effect. (References: C.L. Hannon, E.V. Anslyn, Bioorganic Chemistry Frontiers, Springer-Verlag: Berlin, Heidelberg, 1993, vol3, 193.). Guanidine is one of the most basic neutral nitrogen compounds, and its derivatives are widely used in organic synthesis as catalysts of strong organic bases. (References: Y. Yamamoto, S. Kojima, In The Chemistry of Amidines and Imidates; S. Patai, Z. Rappoport, Eds, John Wiley & Sons Inc.: New York, 1991, vol2, pp485.). [0003] [0004] (I) [0005] Six-membered bicyclic guanidine (MTBD) is an effective organic ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04
Inventor 叶伟平肖诗华徐俊烨
Owner RAFFLES PHAMRMATECH CO LTD
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