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Synthesis of 2-(2, 5-dimethoxy-phenyl)-ethylamine

Author: WangZuo
Tutor: ZhangZhengBo
School: Huazhong University of Science and Technology
Course: Organic Chemistry
Keywords: 2-(2,5-dimethoxy-phenyl)-ethylamine Friedel-Crafts acylation reaction Delepine reaction Trifluoromethane sulfonate
CLC: TQ246.31
Type: Master's thesis
Year: 2008
Downloads: 138
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Abstract


Phenylethylamine and its ramification are very important drug intermediates. For example, they can be used to synthesize the drug for cure arrhythmia, hypertension, cancer, ischemic heart disease. They can also be used to prepare anti-tension agent and calcium antagonist. Up to now, we usually get them by aroma-formaldhyde, ethylic of cyanogen, methyl of chlorine, cyanide-deoxidize and propyldiacid methods. But these ways,more or less, exist problems of toxicity, low yield ,high cost and serious environmental pollution. So, there are great needs to explore a new way which is environment-friendly and low-cost to synthesize phenylethylamine and its ramification.This paper explored a new synthetic routes of 2-(2,5-dimethoxy-phenyl)-ethylamine. Firstly we prepared the 2-chloro-1-(2,5-dimethoxy-phenyl)-ethanone through Friedel- Crafts acylation reactions between 1,4-dimethoxy-benzene and chloro-acetyl chloride. Halogen replacement reaction involved sodium iodide and Delepine reaction involved hexamethylenetetramine were taken in turn to synthesize 2-(2,5-dimethoxy-phenyl) -2-oxo-ethyl-ammonium iodide. We got a satisfactory result in the first two steps. Lastly we tried to prepare 2-(2,5-dimethoxy-phenyl)-ethylamine though Wolff-Kishner-Huang Minlon reaction but failed.Trifluoromethane sulfonate (M(OTf)n,M=metal,OTf= Trifluoromethane sulfonic, n=coordinate number) is a kind of novel Lewis aicd catalyst. This paper studied the catalytic activity of Cu(OTf)2、Zn(OTf)2、Yb(OTf)3、Sm(OTf)3 in the Friedel-Crafts acylation of 1,4-dimethoxy-benzene and chloroacetyl chloride respectively. But they all did not well on the condition.

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CLC: > Industrial Technology > Chemical Industry > Basic Organic Chemistry Industry > The production of aromatic compounds > Aromatic nitrogen compounds > Aromatic amines and their derivatives > Aromatic amines
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