55379-74-3

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 68-12-2 N,N-dimethyl-formamide 
• 151-50-8 potassium cyanide 
• 124-40-3 dimethyl amine 
• 50353-47-4 phenyl acetaldehyde cyanohydrin 
• 103-82-2 phenylacetic acid 

Downstream Products

• 6319-84-2 bibenzyl-α-yl-dimethyl-amine 
• 1126-71-2 N,N-dimethylphenethylamine 
• 2576-14-9 (1-benzyl-propyl)-dimethyl-amine 

Relevant academic research and scientific papers

One-Pot Synthesis of α-Amino Nitrile Units through Alkylative Strecker Cyanation from Formamides

In this work, we describe the one-pot synthesis of α-amino nitrile units by the concomitant addition of alkyl (or aryl) Grignard reagents and TMS cyanide through alkylative Strecker cyanation from readily available formamides. The reaction is broad in sco

Direct Catalytic Reductive N-Alkylation of Amines with Carboxylic Acids: Chemoselective Enamine Formation and further Functionalizations

Direct reductive N-alkylation of secondary amines with carboxylic acids using molybdenum hexacarbonyl (5 mol %) as catalyst and diethoxymethylsilane as reducing agent generate enamines in a straightforward fashion in high yields. The formed enamines are without the need for isolation or purification further reacted with trimethylsilyl cyanide in the same reaction flask to yield α-amino nitriles in good yields. In the optimized reaction conditions equimolar amounts of carboxylic acid and amine are reacted under neat conditions, and a catalytic amount of trifluoroethanol (0.1 mol %) is added along with TMSCN for the cyanation step. The reductive N-alkylation reaction is demonstrated to be highly chemoselective, tolerating a multitude of different functional groups present in the starting carboxylic acids and amines. The reaction is scalable and the generated α-amino nitriles are converted to other useful compounds, e.g., α-amino acids or amino-tetrazoles. In addition, the intermediate enamines are further transformed into triazolines, sulfonylformamidines, pyrimidinediones, and TMS-propargylamines, respectively, in high yields under mild reaction conditions. Benzoic acids react with secondary amines under similar conditions to give tertiary amines in high yields, and using this methodology, the biologically active compound Piribedil was isolated in 80% yield in a direct one-pot reaction setup.