5663-91-2

Upstream product

• 111-86-4 n-Octylamine 
• 60-12-8 2-phenylethanol 
• 629-05-0 n-octyne 
• 64-04-0 phenethylamine 
• 128297-88-1 N-octyl-N-(2-phenyl-ethyl)-amino-acetonitrile 

Downstream Products

• 128297-95-0 Octyl-phenethyl-amine; hydrochloride 

Relevant academic research and scientific papers

Rhodium-Catalyzed Anti-Markovnikov Hydroamination of Aliphatic and Aromatic Terminal Alkynes with Aliphatic Primary Amines

Anti-Markovnikov hydroamination of both aliphatic and aromatic terminal alkynes with primary amines was achieved using an 8-quinolinolato rhodium catalyst to form aldimines and enamines in high yields. This catalytic system realized high functional group tolerance including hydroxy, bromo, cyano, and thioester groups.

Direct N-alkylation of amines with alcohols using AlCl3 as a Lewis acid

A substitution reaction of amines with alcohols for N-alkylated amines has been developed using inexpensive AlCl3 without any ligand or additive. Either aromatic or aliphatic amines and primary or secondary alcohols perform the AlCl3-mediated reaction smoothly to afford various N-alkylated amines in satisfactory yields.

Selective alkylation of amines with alcohols by Cp*- iridium(III) half-sandwich complexes

[Cp*Ir(Pro)Cl] (Pro = prolinato) was identified among a series of Cp*-iridium half-sandwich complexes as a highly reactive and selective catalyst for the alkylation of amines with alcohols. It is active under mild conditions in either toluene or water without the need for base or other additives, tolerates a wide range of alcohols and amines, and gives secondary amines in good to excellent isolated yields.

Cp*Ir-catalyzed N-alkylation of amines with alcohols. A versatile and atom economical method for the synthesis of amines

A versatile and highly atom economical catalytic system consisting of [Cp*IrCl2]2/NaHCO3 (Cp*=pentamethylcyclopentadienyl) for the N-alkylation of amines with primary and secondary alcohols as alkylating reagents has been developed. For example, the reaction of equimolar amounts of aniline and benzyl alcohol in the presence of [Cp*IrCl2]2 (1.0 mol % Ir) and NaHCO3 (1.0 mol %) in toluene at 110 °C gives N-benzylaniline in 94% yield. The present catalytic system is applicable to the N-alkylation of both primary and secondary amines, and only harmless water is produced as co-product. A wide variety of secondary and tertiary amines can be synthesized with high atom economy under mild and less-toxic conditions. One-pot sequential N-alkylation leading to tertiary amines bearing three different substituents is also described.

N-Alkylation of amines with alcohols catalyzed by a Cp*Ir complex

A new effective catalytic system consisting of [Cp*IrCl2]2/K2CO3 (Cp=pentamethylcyclopentadienyl) for the N-alkylation of primary amines with alcohols has been developed. As an example, the reaction of aniline with benzyl alcohol in the presence of [Cp*IrCl2]2 (5.0 mol%Ir) and K2CO3 (5.0 mol%) in toluene at 110°C for 17 h gave benzylaniline in an isolated yield of 88%.

Mono-N-alkylation of α-Aminoacetonitriles. A Novel Route to Unsymmetrical Secondary Amines

Mannich-type condensation products of an aldehyde with an α-aminoacetonitrile and benzotriazole are treated with sodium borohydride or with a Grignard reagent to give unsymmetrical N,N-dialkylaminoacetonitriles, which, on decyanomethylation provide unsymmetrical secondary amines.