New method for preparing tyramine

A technology for tyramide and decarboxylation reaction, which is applied in chemical instruments and methods, preparation of organic compounds, preparation of aminohydroxy compounds, etc., can solve the problems of unsuitability for industrial production, poor product quality, low reaction yield, etc., and achieves easy industrialization. The effect of production, good quality and high yield

Active Publication Date: 2013-06-26
SHANGHAI PUYI CHEM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

1998 (38) 4.58~59) adopt the direct decarboxylation of phenyl ether at high temperature, the reaction yield is low, the energy consumption is high, the pollution is large, many products denature, and the product quality is poor; Burton etc. (Burton, H.Hu, P.F.Investigation of Wada's method of converting α-amino acids into 2-substituted ethylamines.Journal of the Chemical Society (1949), 181-2) adopts diphenylamine as solvent, and thiourea participates in the reaction, the overall yield is low, the pollution is large, and the cost is high; Waser (Waser, ( Battersby, Alan R.; Chrystal, Ewan J.T.; Staunton, James. Studies of enzyme-mediated reactions. Part 12. Stereochemical course of the decarboxylation of (2S)-tyrosine to tyramine by microbial, mammalian, and plant systems. Journal of the Chemical Society , PerkinTransactions 1: Organic and Bio-Organic Chemistry (1972~1999) (1980), (1), 31~42; Lippoldt, A.; Bode, R.; Birnbaum, D.Sekt.Biol., Degradation of aromatic amino acids in Candida maltosa. Journal of Basic Microbiology (1986), 26(3), 145-54; Nakazawa, Hidetsugu; Sano, Konosuke; Matsuda, Keizo; Mitsugi, Koji. Enzymic preparation of aromatic ethylamines from aromatic L- amino acids.Bioscience, Biotechnology, and Biochemistry (1993), 57(7), 1210-11) all adopt bio-enzyme conversion technology, which is not conducive to industrial mass production
[0006] Therefore, the above routes are either that the steps are more complicated or that the yield is lower.
or require the use of expensive catalysts

Method used

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  • New method for preparing tyramine

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Add 10 g of tyrosine, 6 g of diisoamyl ketone, and 20 g of cyclohexanol into a 100 mL reaction flask, pass through nitrogen to protect and raise the temperature to reflux (the temperature is between 140 and 150° C.), and remove the generated water in time. React until the solution turns into a brownish-red transparent liquid (about 4-6 hours). After cooling the reaction liquid, add 25 g of water, stir overnight with nitrogen gas, add 8 g of ether, stir, filter with suction, and rinse with 6 g of methanol to obtain the product. Vacuum dried to obtain 4.9 g of white tyramide product, content: 98.4%. Yield 64.4%. MP: 161-162°C (Waser, E. Phenylalanine series. VI. Decarboxylation of tryosine andleucine. Helvetica Chimica Acta (1925), 8758-73, 164-165°C). MS(EI): m / e=137; IR(KBr)cm -1 : 3330, 3300, 1600, 1520, 1260, 820. It is completely consistent with the Sadtler standard spectrum (spectrum number 18175K); 1 HNMR (500MHZ, CDCl3): δppm: 3.3-3.5 (4H, -CH2-CH2-, t); 7.4-7....

Embodiment 2

[0032] Add 10 g of tyrosine and 20 g of diisoamyl ketone into a 100 mL reaction flask, pass through nitrogen to protect and raise the temperature (the temperature is between 160 and 170° C.), and remove the generated water in time. React until the solution turns into a brown-red transparent liquid (about 3 to 5 hours). After cooling the reaction liquid, add 25 g of water, stir overnight with nitrogen gas, add 8 g of ether, stir, filter with suction, and rinse with 6 g of methanol to obtain the product. Vacuum dried to obtain 5.5 g of white tyramide product, content: 98.1%. Yield 68.4%. MP: 162-164°C.

Embodiment 3

[0034]Add 10g of tyrosine, 13g of cyclohexanol, and 5g of acetophenone into a 100mL reaction flask, pass through nitrogen to protect and raise the temperature to reflux (the temperature is between 160-170°C), and remove the generated water in time. React until the solution turns into a brownish-red transparent liquid (about 2 to 3 hours). After cooling the reaction liquid, add 25 g of water, stir overnight with nitrogen, add 8 g of ether, stir, filter with suction, and rinse with 6 g of methanol to obtain the product. Vacuum dried to obtain 5.2 g of white tyramide product, content: 99.4%. Yield 72.3%. MP: 163-164°C.

[0035] The present invention adopts the decarboxylation process of ketone-catalyzed amino acid, which greatly reduces the decarboxylation temperature from 255-260 to 140-170 degrees, improves the yield of the product, and avoids the problems of denaturation and color depth of the product at high temperature. After simple washing, a white high-purity product tyr...

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Abstract

The invention provides a new method for preparing tyramine. In the new method, tyramine with structural formula III is prepared by performing a catalytic decarboxylation reaction on tyrosine with structural formula I and a decarboxylation catalyst with structural formula II in organic solvent, wherein R1 and R2 are alkyl or aryl respectively; preferably, the alkyl is straight chain or branched chain hydrocarbon containing 1 to 6 carbon atoms, the aryl is 6-carbon monocyclic, 10-carbon dicyclic and 14-carbon tricyclic aromatic ring groups, the organic solvent is the decarboxylation catalyst, alcohols or aromatic hydrocarbon, the temperature of the catalytic decarboxylation reaction is between 140 and 170 DEG C, and the decarboxylation catalyst is saturated ketone; and in the catalytic decarboxylation reaction, a water division device is adopted, and nitrogen is used for protection; and after the catalytic decarboxylation reaction is finished, water is added for hydrolysis, and the tyramine is subjected to conventional post-processing so as to obtain pure tyramine. The new method has the advantages of novel synthetic route, mild operating condition, low cost, high yield, environmental friendliness and easy industrial batch production, and has high economic and social benefits.

Description

technical field [0001] The invention relates to the technical field of compound preparation, in particular to the technical field of catalytic decarboxylation, and more specifically to a new method for preparing tyramine. Background technique [0002] The chemical name of tyramine is 4-hydroxyphenylethylamine, which is an important intermediate in the synthesis of drugs, and can also be used as a biochemical reagent, as well as a drug for treating migraine and diagnosing pheochromocytoma. Tyramine occurs naturally in some mistletoe trees and in decaying animal tissues. [0003] The earliest chemical synthesis of tyramine was reported by Sckmitt and Nass. The synthesis of tyramine mainly includes phenylacetonitrile (Barger G, Walpole GS. Further syntheses of p-hydroxyphenylethylamine. J Chem Soc. 1909, 95: 1720-1724), 2-Phenylbromoethane (Slotta KH.Altner W.A new tyramine synthesis.Ber.1931.64B: 1510) and phenethylamine are the electrophilic substitution reaction routes of r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C215/52C07C213/08B01J31/02
Inventor 王博
Owner SHANGHAI PUYI CHEM CO LTD
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