Synthesis method of 2-(1-cyclohexenyl) ethylamine

A technology of cyclohexenyl and synthesis method, applied in the field of synthesis of compound 2-ethylamine, can solve the problems of difficult industrial implementation, harsh reaction conditions, long process route and the like
CN111807968AActive Publication Date: 2020-10-23FUDAN UNIV
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Patent Information

Authority / Receiving Office
CN · China
Current Assignee / Owner
FUDAN UNIV
Publication Date
2020-10-23

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Abstract

The invention belongs to the technical field of organic chemistry, and particularly relates to a synthesis method of a compound 2-(1-cyclohexenyl) ethylamine (I). Cyclohexanone (II) and a Grignard reagent are subjected to a Grignard reaction in an organic solvent to be converted into 1-vinyl cyclohexanol (III), the 1-vinyl cyclohexanol (III) and a chlorination reagent are subjected to a chlorination / rearrangement one-pot reaction in an organic solvent in the presence of organic alkali to prepare (2-chloroethylene methylene) cyclohexane (IV), the (2-chloroethylene methylene) cyclohexane (IV) and urotropine are subjected to quaternization in an organic solvent to form N-cyclohexylidene ethyl urotropine hydrochloride (V), and finally, hydrolysis rearrangement is carried out in a solvent in the presence of inorganic mineral acid to obtain the 2-(1-cyclohexenyl) ethylamine (I). The compound (I) has important industrial application value as an intermediate for synthesizing the antitussive drug dextromethorphan hydrobromide. The method has the advantages of cheap and accessible raw materials, mild reaction conditions, high yield and high product purity, is simple to operate, and is convenient for industrial production.
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Description

technical field

[0001] The invention belongs to the technical field of organic chemistry, in particular to a synthesis method of compound 2-(1-cyclohexenyl)ethylamine. Background technique

[0002] The structural formula of compound 2-(1-cyclohexenyl) ethylamine is:

[0003]

[0004] Denoted as compound (I). The compound (I) is an important intermediate for synthesizing the antitussive drug dextromethorphan hydrobromide (Dextromethorphan Hydrobromide). Chinese patents CN 107011178 and CN 108558673 respectively describe the method of preparing the compound (I) by catalytic hydrogenation of 2-(1-cyclohexenyl) acetonitrile with Pd / C or Raney nickel. This method has poor regioselectivity, many by-products, difficult separation and low yield. Chinese patent CN 105669465 discloses a process for preparing compound (I) by catalyzing the hydrogenation of 2-(1-cyclohexenyl) acetonitrile at 1200-1300° C. using one or both of noble metals hafnium, vanadium and niobium. The method...

Claims

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