Application of the ionic iron (III) complex as catalyst in preparation of benzylamine compound

Patent metadata

Field	Value
Publication number	US-11890602-B2
Application number	US-202117239496-A
Country	US
Kind code	B2
Filing date	Apr 23, 2021
Priority date	Oct 29, 2018
Publication date	Feb 6, 2024
Grant date	Feb 6, 2024

Abstract

Disclosed is an application of an ionic iron (III) complex as a catalyst in preparation of a benzylamine compound, that is, an ionic iron (III) complex having a molecular formula of [(RNCHCHNR)CH][FeBr4] (R is tert-butyl) and containing 1,3-di-tert-butyl imidazolium cation is used as a catalyst, di-tert-butyl peroxide is used as an oxidizing agent, and a benzylamine compound is synthesized by oxidation reaction of a toluene/ethylbenzene compound with an aromatic amine. The present invention has a wide application range, and is applicable not only to a toluene compound containing a benzylic primary carbon-hydrogen bond but also to an ethylbenzene compound containing a benzyl secondary carbon-hydrogen bond. This is the first example of the preparation of a benzylamine compound by oxidation reaction of a toluene/ethylbenzene compound and an aromatic amine by an iron-based catalyst.

First claim

The invention claimed is:

1. A method for preparing a catalyst for preparing a benzylamine compound comprising:
adding 1,3-di-tert-butylimidazole bromide into a tetrahydrofuran solution of ferric tribromide,
reacting at 60° C. for 24 h,
removing tetrahydrofuran under vacuum,
washing with hexane,
drying and extracting with tetrahydrofuran,
centrifugating to collecting a supernatant, and
adding hexane to the supernatant to precipitate the catalyst at room temperature as a red brown crystal,
wherein the catalyst is an ionic iron (III) complex having the following structure:

Assignees

• Univ Soochow

Inventors

• Sun Hongmei
• Li Ruipeng

Classifications

• B01J31/22 Primary

  Organic complexes · CPC title

• B01J37/08

  Heat treatment {(B01J37/0009, B01J37/0018 take precedence)} · CPC title

• B01J37/12

  Oxidising · CPC title

• B01J31/16 Primary

  containing coordination complexes · CPC title

• C07C209/60

  by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes · CPC title