CN101973889B - Method for preparing and synthesizing chiral (R)-alpha-phenethylamine hydrochloride - Google Patents
Method for preparing and synthesizing chiral (R)-alpha-phenethylamine hydrochloride Download PDFInfo
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- CN101973889B CN101973889B CN 201010518306 CN201010518306A CN101973889B CN 101973889 B CN101973889 B CN 101973889B CN 201010518306 CN201010518306 CN 201010518306 CN 201010518306 A CN201010518306 A CN 201010518306A CN 101973889 B CN101973889 B CN 101973889B
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- alpha
- hydrochloride
- phenylethylamine
- phenethylamine
- compound
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Abstract
The invention provides a novel chiral (R)-alpha-phenethylamine hydrochloride compound. The method for synthesizing the compound comprises the following steps: allowing (R)-alpha-phenethylamine to react with samarium(III) chloride hexahydrate for 1 day in absolute tetrahydrofuran solution; and thermally filtering the reacting fluid to naturally volatilize filtrate so as to obtain the product chiral (R)-alpha-phenethylamine hydrochloride. The compound shows excellent catalytic performance in a cyanosilicone reaction of benzaldehyde, with yield reaching as high as 98 percent.
Description
One, technical field
The present invention relates to a kind of preparation and synthetic method of quaternary ammonium salt, is exactly a kind of preparation and synthetic method of chirality α-phenylethylamine hydrochloride.
Two, background technology
The synthetic method of quaternary ammonium salt has many bibliographical informations.As far back as 1956, J.Chem.Soc. reported the synthetic method of some quaternary ammonium salts, and nineteen fifty-nine, J.Am.Chem.Soc. has also reported the synthetic method of quaternary ammonium salt.(1.Surrey，Alexander?R.；Lesher，George?Y.；Mayer，J.Richard；Webb，Wm.G.Journal?of?the?American?Chemical?Society(1959)，81?2894-7；2.Davis，M.Journal?of?the?Chemical?Society(1956)，337-43.)。
The applicant does not obtain the target product title complex in the experiment of synthesis of chiral (R)-α-phenylethylamine and six hydration Samarium chloride title complexs, but obtained another kind of novel chiral compound (R)-α-phenylethylamine hydrochloride.
Three, summary of the invention
The present invention aims to provide chipal compounds (R)-α-phenylethylamine hydrochloride, and technical problem to be solved is that one-step synthesis obtains target product.
The alleged a kind of chirality (R) of the present invention-α-phenylethylamine hydrochloride be by (R)-α-phenylethylamine and the preparation of six hydration Samarium chlorides by the compound shown in following chemical formula:
Chemical name: (R)-α-phenylethylamine hydrochloride, be called for short compound (I).
This synthetic method comprises synthesizes and separates, (R)-α-phenylethylamine and the six hydration Samarium chlorides of described synthetic 2.38: 1 reacted in anhydrous tetrahydrofuran solution one day, with the reaction solution heat filtering, naturally volatilization filtrate, obtain product chirality (R)-α-phenylethylamine hydrochloride clear crystal.
One step of this synthetic method obtains target product, and technique is simple, and is easy to operate.
Four, description of drawings
Fig. 1 is the X-diffraction analysis figure of (R)-α-phenylethylamine hydrochloride.
Five, embodiment
1. the preparation of chirality (R)-α-phenylethylamine hydrochloride
In the 100mL flask, under the anhydrous and oxygen-free condition, add six hydration Samarium chloride 0.74g (2mmol), (R)-α-phenylethylamine 0.6mL (4.76mmol), anhydrous tetrahydro furan 30mL is with the mixture 24h that refluxes, stopped reaction, the reaction solution heat filtering, volatilization filtrate, obtain product chirality (R)-α-phenylethylamine hydrochloride clear crystal naturally.Fusing point: 118-120 ℃, results of elemental analyses is as follows: theoretical value: C, 60.95%; H, 7.676%; N, 8.886%, measured value: C, 59.36%; H, 7.445%; N, 8.698%.
2. the nitrile silicification reaction is used
The preparation of 2-phenyl-2-(three silyloxies) propionitrile
0.20mmol Compound I, phenyl aldehyde 0.1mL, TMSCN 0.3ml (3.3mmol) adds under 20～30 ℃ in succession, after 19h, add shrend go out after the post layer (sherwood oil/methylene dichloride: 5/1), get colourless oil liquid, productive rate: 98%,
1H NMR (300MHz, CDCl3) 7.56-7.59 (m, 0.9Hz, 2H), 7.31-7.34 (m, 3H), (5.43 s, 1H), 0.16 (s, 9H) .13CNMR (75MHz, CDCl3) 136.1,128.8 (x2), 126.2 (x2), 119.1,63.5 ,-0.39 (x3).
Claims (1)
1. the synthetic method of a chirality (R)-α-phenylethylamine hydrochloride, comprise and synthesize and separate, (the R)-α-phenylethylamine and the six hydration Samarium chlorides that it is characterized in that 2.38: 1 reacted in anhydrous tetrahydrofuran solution one day, with the reaction solution heat filtering, naturally volatilization filtrate, obtain product chirality (R)-α-phenylethylamine hydrochloride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN 201010518306 CN101973889B (en) | 2010-10-25 | 2010-10-25 | Method for preparing and synthesizing chiral (R)-alpha-phenethylamine hydrochloride |
Applications Claiming Priority (1)
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| CN 201010518306 CN101973889B (en) | 2010-10-25 | 2010-10-25 | Method for preparing and synthesizing chiral (R)-alpha-phenethylamine hydrochloride |
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| Publication Number | Publication Date |
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| CN101973889A CN101973889A (en) | 2011-02-16 |
| CN101973889B true CN101973889B (en) | 2013-06-12 |
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| CN 201010518306 Expired - Fee Related CN101973889B (en) | 2010-10-25 | 2010-10-25 | Method for preparing and synthesizing chiral (R)-alpha-phenethylamine hydrochloride |
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Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102329240A (en) * | 2011-07-01 | 2012-01-25 | 罗梅 | Method for preparing and synthesizing m-xylylenediamine dihydrochloride |
| CN103804199B (en) * | 2014-02-25 | 2016-04-13 | 罗梅 | Synthesis method of chiral alpha-phenylethylamine hydrochloride |
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2010
- 2010-10-25 CN CN 201010518306 patent/CN101973889B/en not_active Expired - Fee Related
Non-Patent Citations (2)
| Title |
|---|
| Enantioselective Hydrogenation of N-H Imines;Yongkui et al;《Journal of the American Chemical Society》;20090701;第131卷(第29期);9882-9883 * |
| Yongkui et al.Enantioselective Hydrogenation of N-H Imines.《Journal of the American Chemical Society》.2009,第131卷(第29期),9882-9883. |
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| CN101973889A (en) | 2011-02-16 |
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Granted publication date: 20130612 Termination date: 20131025 |