A kind of synthetic method of 2-(1-cyclohexenyl) ethylamine

A technology of cyclohexenyl and synthetic method, which is applied in the field of compound 2-ethylamine synthesis, can solve the problems of high yield, high cost, difficult industrial implementation, etc.

Active Publication Date: 2022-05-20
FUDAN UNIV
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  • 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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  • A kind of synthetic method of 2-(1-cyclohexenyl) ethylamine
  • A kind of synthetic method of 2-(1-cyclohexenyl) ethylamine
  • A kind of synthetic 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, in particular to a synthetic method of compound 2-(1-cyclohexenyl)ethylamine (I). The present invention carries out Grignard reaction with cyclohexanone (II) and Grignard reagent in an organic solvent and converts it into 1-vinyl cyclohexanol (III), and then carries out chlorination with a chlorination reagent in an organic solvent in the presence of an organic base. Generation / rearrangement one-pot reaction to prepare (2-chloroethylmethylene)cyclohexane (IV), and then carry out quaternization with urotropine in an organic solvent to form N-cyclohexylidene ethyl urotropine Hydrochloride (V), and finally carry out hydrolysis and rearrangement in a solvent in the presence of inorganic mineral acid to obtain 2-(1-cyclohexenyl)ethylamine (I). Compound (I) is an intermediate in the synthesis of antitussive drug dextromethorphan hydrobromide, and has important industrial application value. The method of the invention has cheap and easy-to-obtain raw materials, mild reaction conditions, simple and convenient operation, high yield and product purity, and is convenient for industrialized 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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Patent Type & Authority Patents(China)
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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