N-[Amino(imino)methyl]-4-methylpiperazine-1-carboximidamide synthesis

Yield:18413-26-8 54%

Reaction Conditions:

Stage #1: 1-methyl-piperazine;N-Cyanoguanidine in toluene at 20; for 0.25 h;
Stage #2: with hydrogenchloride in water;toluene; for 7 h;

Steps:

2.2. General Procedure for the Synthesis of Compounds 1-10.

General procedure: To a solution of dicyandiamide (0.5 g, 0.0060 mol) intoluene (5 mL) was added 1.1 mol equiv of correspondingalkylamines - or arylamines -. After the reactionmixture was stirred at room temperature for 15min, amixture 50 : 50 of HCl diluted in water (2.5 mL) was addeddropwise. This mixture was stirred at reflux for 3 to 16 h.After that, the obtained residuewas neutralizedwith a dilutedsolution of NH4OH. Solvent was removed under vacuum,and the residues were washed with water. The crude solidproducts were then recrystallized from ethanol affording titlecompounds (Figure 2, Table 1).

References:

Gutierrez-Lara, Erika;Martínez-Conde, Carlos;Rosales-Ortega, Edgar;Ramírez-Espinosa, Juan José;Rivera-Leyva, Julio C.;Centurión, David;Carvajal, Karla;Ortega-Cuellar, Daniel;Estrada-Soto, Samuel;Navarrete-Vázquez, Gabriel [Journal of Chemistry,2017,vol. 2017,art. no. 1212609]