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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

Active Publication Date: 2020-10-23
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method is carried out at high temperature, the reaction conditions are harsh, and the energy consumption is high
Chinese patent CN 10882197 uses red aluminum to catalyze the hydrogenation of 2-(1-cyclohexenyl) acetonitrile to obtain compound (I), and the yield is relatively high. The disadvantage is that the catalyst used is expensive and difficult to implement industrially.
The process route is long, and expensive aluminum tetrahydrogen lithium is still used as the reducing agent, and the cost is high

Method used

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  • Synthesis method of 2-(1-cyclohexenyl) ethylamine
  • Synthesis method of 2-(1-cyclohexenyl) ethylamine
  • Synthesis method of 2-(1-cyclohexenyl) ethylamine

Examples

Experimental program
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Effect test

Embodiment 1

[0042] Example 1: The compound cyclohexanone (II, 9.8g, 0.1mol) was mixed with 200mL tetrahydrofuran, and after cooling to 0°C in an ice bath, a tetrahydrofuran solution of vinylmagnesium chloride (1.6M, 100mL) was added, and stirred at room temperature for 10 hours After quenching with a saturated ammonium chloride solution, the organic phase was separated, the aqueous phase was extracted twice with ethyl acetate, and the organic phases were combined and concentrated to obtain 12.4 g of crude product of 1-vinylcyclohexanol (III).

Embodiment 2

[0043] Example 2: The compound cyclohexanone (II, 9.8g, 0.1mol) was mixed with 200mL tetrahydrofuran, and after cooling to 0°C in an ice bath, a tetrahydrofuran solution (1M, 150mL) of vinylmagnesium bromide was added, and stirred at room temperature for 6 Quenched with ammonium chloride saturated solution after 1 hour, separated the organic phase, extracted the aqueous phase twice with ethyl acetate, combined the organic phases, and concentrated it to obtain 12.6 g of the crude product of 1-vinylcyclohexanol (III) .

[0044] Two, the preparation of (2-chloroethylmethylene) cyclohexane (IV)

[0045] Example 1: 12.6g of 1-vinylcyclohexanol (III, 12.6g, 0.1mol) prepared in the previous step was mixed with 150mL of tetrahydrofuran, and after ice bathing to 0°C, pyridine (14.22g, 0.18mol) and Thionyl chloride (18.88g, 0.16mol), after stirring the reaction for 45min, 3 The saturated solution was quenched, the organic phase was separated, the aqueous phase was extracted twice with...

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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.

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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Application Information

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IPC IPC(8): C07C209/62C07C211/25C07C29/40C07C35/17C07C17/358C07C22/00C07D487/18
CPCC07C209/62C07C29/40C07C17/358C07D487/18C07C2601/16C07C2601/14C07C211/25C07C35/17C07C22/00C07C17/16C07C23/10C07C17/013C07C29/38
Inventor 陈芬儿李祉宁程荡黄则度姜梅芬陶媛
Owner FUDAN UNIV
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