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Preparation method of N-substituted ethylene diamine derivative
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A derivative, ethylenediamine technology, applied in the field of preparation of fine chemicals, can solve the problem of expensive 2-oxazolinone, and achieve the effects of high total yield, stable reaction and mild conditions
Inactive Publication Date: 2009-12-30
HEFEI UNIV OF TECH
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[0006] In 1992, Graham S et al. (J.Org.Chem., 1991,57 (23): 6257-6265) used 2-oxazolone as raw material to generate N-phenylethylenediamine under the reflux of n-hexanol as solvent. The rate is 78%, but the raw material 2-oxazolinone is more expensive
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Embodiment 1
[0019]
[0020] (1), the preparation of intermediate (I) a: add water (60ml), FeCl successively in 150ml there-necked flask 3 .6H 2 O (0.97g, 6mmol), imidazole (4.1g, 60mmol), ethyl acrylate (7.7ml, 72mmol) was slowly added dropwise, stirred, reacted at 30°C for 15h, column chromatography (CH 2 Cl 2 :CH 3 OH=40:1) isolated light yellow liquid compound (I)a (9.4g), yield 94.8%, 1 NMR (Cl 3 CD-d 6 )δ: 7.50(s, 1H), 7.04(s, 1H), 6.94(s, 1H), 4.26(t, 2H), 4.13(q, 2H), 2.77(t, 2H), 1.24(t, 3H ).
[0021] (2), the preparation of intermediate (II) a: 80% hydrazine hydrate (7.5ml, 150mmol), ethanol (30ml), slowly add dropwise ethanol (10ml) and intermediate (I) a (8.40g, 50mmol) The temperature of the mixture was not higher than 40°C. After stirring for about 30 minutes, the temperature was raised to reflux for 8 hours. Column chromatography (CH 2 Cl 2 :CH 3 OH=20:3) to obtain yellow compound (II)a (7.26g) with a yield of 94.3%. 1 HNMR (Cl 3 CD-d 6 )δ: 8.41(s, 1H), 7.52...
Embodiment 2
[0024]
[0025] According to the method for Example 1, benzylamine was used instead of imidazole to prepare (III)b, with a total yield of 72.1% (calculated as ethyl acrylate), 1 HNMR (Cl 3 CD-d 6 ) δ: 7.30 (m, 5H), 3.79 (t, 2H), 2.74 (m, 2H), 1.46 (m, 2H).
Embodiment 3
[0027]
[0028] According to the method for Example 1, (III)c was prepared with aniline instead of imidazole, with a total yield of 60.4% (calculated as ethyl acrylate), 1 HNMR (Cl 3 CD-d 6 )δ: 7.14(m, 2H), 6.67(m, 2H), 6.58(m, 1H), 4.10(s, 1H), 3.07(m, 2H), 2.82(m, 2H), 1.30(s, 2H ).
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Abstract
The invention discloses a synthetic method of an N-substituted ethylenediamine derivative as structure fragments for various drugs. The method comprises the following steps: first performing Michael addition reaction on aromatic amine or fatty amine or heterocyclic amine and ethyl acrylate, then performing hydrazinolysis, and finally performing Curtius rearrangement reaction, thus preparing the target compound. The method has the advantages of low cost, moderate conditions, easy operation, high total yield and the like.
Description
1. Technical field [0001] The present invention relates to a preparation method of a class of fine chemicals, in particular to a preparation method of pharmaceutical intermediates, in particular to a synthesis method of N-substituted ethylenediamine derivatives as structural fragments of various medicines. 2. Background technology [0002] N-substituted ethylenediamine derivatives are widely used as intermediates of fine chemicals and as structural fragments of various drugs, such as 2-(1-imidazolyl)ethylamine as N- Structural fragments of alkylsulfonamides (CarlP.Bergstrom et al., Bioorg.Med.Chem.Lett., 2008, 18(2):464-468); 1-(2-aminoethyl)piperidine has Structural fragments for the treatment of central nervous system and intestinal disorders (Nancy Elisabeth Krauss et al., US 7528250, 2009), etc. At present, the synthesis methods of such compounds mainly include the following methods. [0003] In 1977, Richard J.Sundberg et al. (J.Heterocycl.Chem., 1977, 14(7): 1279-81)...
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