Method for preparing benzyl amine compound

Patent metadata

Field	Value
Publication number	US-11873265-B2
Application number	US-202117239500-A
Country	US
Kind code	B2
Filing date	Apr 23, 2021
Priority date	Oct 29, 2018
Publication date	Jan 16, 2024
Grant date	Jan 16, 2024

Abstract

Disclosed is a method for preparing a benzyl amine compound, i.e., synthesizing a benzyl amine compound by means of an oxidation reaction between a methylbenzene/ethylbenzene compound and arylamine by using an ionic iron (III) complex containing 1,3-di-tert-butylimidazolium cation and having a molecular formula of [(RNCHCHNR)CH][FeBr4] (R being tert-butyl) and di-t-butyl peroxide as an oxidant. The present invention is not only applicable to a methylbenzene compound containing a benzylic primary carbon-hydrogen bond but also applicable to an ethylbenzene compound containing a benzylic secondary carbon-hydrogen bond, and therefore is widely applicable. This is the first case where the preparation of a benzyl amine compound by means of an oxidation reaction between a methylbenzene/ethylbenzene compound and arylamine is implemented by an iron catalyst.

First claim

The invention claimed is:

1. A method for preparing a benzylamine compound comprising:
adding an aryl compound, an arylamine, an oxidizing agent, and a catalyst to form a reaction mixture; and
conducting a reaction by heating the reaction mixture to obtain the benzylamine compound,
wherein:
the benzylamine compound has the following structure:

the aryl compound has the following structure:

the arylamine has the following structure:

the oxidizing agent is di-tert-butyl peroxide;
the catalyst is an ionic iron (III) complex having the following structure:

and
R is hydrogen or methyl; R 1 is cyano, nitro, trifluoromethyl or acetyl; and R 2 is hydrogen or methyl; and Ar is phenyl, p-tert-butylphenyl, o-methylphenyl, mesitylphenyl, p-chlorophenyl, o-chlorophenyl, naphthyl, or thienyl.

2. The method of claim 1 , wherein the reaction is conducted with the aryl compound as a reaction solvent.

3. The method of claim 1 , wherein the reaction mixture is heated at 80 to 150° C. for 15 to 60 hours.

4. The method of claim 1 , wherein a molar ratio of the oxidizing agent:the arylamine is 1:1-1.6; and a molar ratio of the catalyst:the arylamine is 1:5-20.

5. The method of claim 4 , wherein the molar ratio of the oxidizing agent:the arylamine is 1:1.5; and the molar ratio of the catalyst:the arylamine is 1:10.

Assignees

• Univ Soochow

Inventors

• Sun Hongmei
• Wang Dan

Classifications

• C07C209/02 Primary

  by substitution of hydrogen atoms by amino groups · CPC title

• B01J31/22

  Organic complexes · CPC title

• C07C211/48

  N-alkylated amines · CPC title

• B01J31/0284 Primary

  of an aromatic ring, e.g. pyridinium · CPC title

• C07D233/58

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms · CPC title