3399-73-3Relevant articles and documents
Synthesis method of 2-(1-cyclohexenyl) ethylamine
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Paragraph 0050-0057, (2020/11/02)
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.
Palladium-Catalyzed Regioselective C-H Iodination of Unactivated Alkenes
Schreib, Benedikt S.,Carreira, Erick M.
supporting information, p. 8758 - 8763 (2019/06/13)
A palladium-catalyzed C-H iodination of unactivated alkenes is reported. A picolinamide directing group enables the regioselective functionalization of a wide array of olefins to furnish iodination products as single stereoisomers. Mechanistic investigations suggest the reversible formation of a six-membered alkenyl palladacycle intermediate through a turnover-limiting C-H activation.
Method for preparing 1-cyclohexene ethylamine by selective reduction
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Paragraph 0037-0042, (2018/11/27)
The invention discloses a method for preparing 1-cyclohexene ethylamine by selective reduction. The method comprises the following steps: (1) dissolving a raw material 1-cyclohexene acetonitrile in asolvent under the protection of inert gas, then slowly dropwise adding a reducing agent vitride solution at a certain temperature, and reacting at a certain temperature after dropwise adding; quenching by dropwise adding a reaction liquid into an alkali aqueous solution, extracting with an organic solvent, drying with a drying agent, carrying out desolvation with an organic phase to obtain a 1-cyclohexene ethylamine crude product; and (2) heating the 1-cyclohexene ethylamine crude product under a certain vacuum condition for distillation purification so as to obtain a 1-cyclohexene ethylaminepure product. the invention has the following advantages: 1, the vitride solution used in the method has lower toxicity and is cheaper and more easily available, thus greatly reducing raw material andoperational costs; 2, reaction steps of the method are few, the intermediate reaction is easy to control, operation is simple, and the method is easy for large-scale production; and 3, purity and yield of the product prepared by the method are high and both can reach 90% and above.