3760-63-2

Upstream product

• 100-47-0 benzonitrile 
• 124-40-3 dimethyl amine 
• 939-52-6 4-chloro-1-phenylbutan-1-one 
• 1202-55-7 4-phenyl-1-(N,N-dimethylamino)butane 
• 120615-47-6 3-dimethylaminopropylmagnesiumbromide 
• 69954-66-1 4-(dimethylamino)butyric acid hydrochloride 
• 71-43-2 benzene 

Downstream Products

• 26307-34-6 4-Dimethylamino-2-benzyl-1-phenylbutan-1-on 
• 26307-37-9 4-Dimethylamino-2-(4-methyl-benzyl)-1-phenyl-butan-1-one 
• 4560-13-8 dimethyl-[2-(2-phenyl-indol-3-yl)-ethyl]-amine 
• 691412-28-9 N,N-dimethyl-2-(5-fluoro-2-phenylindol-3-yl)ethylamine 
• 43018-74-2 1-p-Chlorphenoxy-5-dimethylamino-pentanol-⁽²⁾ 
• 5554-67-6 4-dimethylamino-1-phenyl-butan-1-ol 

Relevant academic research and scientific papers

Remote C(sp3)-H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate

This letter describes the development of a method for selective remote C(sp3)-H oxygenation of protonated aliphatic amines using aqueous potassium persulfate. Protonation serves to deactivate the proximal C(sp3)-H bonds of the amine substrates and also renders the amines soluble in the aqueous medium. These reactions proceed under relatively mild conditions (within 2 h at 80 °C with amine as limiting reagent) and do not require a transition metal catalyst. This method is applicable to a variety of types of C(sp3)-H bonds, including 3°, 2°, and benzylic C-H sites in primary, secondary, and tertiary amine substrates.

Iron-catalyzed oxyfunctionalization of aliphatic amines at remote benzylic C-H sites

We report the development of an iron-catalyzed method for the selective oxyfunctionalization of benzylic C(sp3)-H bonds in aliphatic amine substrates. This transformation is selective for benzylic C-H bonds that are remote (i.e., at least three carbons) from the amine functional group. High site selectivity is achieved by in situ protonation of the amine with trifluoroacetic acid, which deactivates more traditionally reactive C-H sites that are α to nitrogen. The scope and synthetic utility of this method are demonstrated via the synthesis and derivatization of a variety of amine-containing, biologically active molecules.