Reaction #463513

Reaction equation

N-[methylsulfanyl-(4-(pyridin-2-yl)piperazin-1-yl)methylene]-benzamide

N1-(4-bromobenzyl)-N1-(pyridin-2-yl)-propane-1,3-diamine

→

N-[[3-[N-(4-bromo-benzyl)-N-(pyridin-2-yl)amino]propylamino]-(4-pyridin-2-yl-piperazin-1-yl) methylene]benzamide

Yield 56.5%

Solvents

pyridine

Conditions

Workup

1. 1
   Temperaturethe reaction mixture was heated
2. 2
   Temperatureat reflux for 18 h
3. 3
   OtherThe volatiles were evaporated in vacuo
4. 4
   workup.DISSOLUTIONthe residue dissolved in dichloromethane (100 ml)
5. 5
   Otherevaporated in vacuo
6. 6
   OtherThe residue was purified by column chromatography on silica gel (600 ml)
7. 7
   workup.ADDITIONa mixture of ethyl acetate/triethylamine 95:5 (1 l)
8. 8
   workup.ADDITIONfollowed by a mixture of ethyl acetate/methanol/triethylamine 90:5:5 as eluents

Procedure

To a mixture of N-[methylsulfanyl-(4-(pyridin-2-yl)piperazin-1-yl)methylene]-benzamide (2.9 g, 8.52 mmol) in pyridine (50 ml) was added N1-(4-bromobenzyl)-N1-(pyridin-2-yl)-propane-1,3-diamine (3 g, 9.37 mmol) and the reaction mixture was heated at reflux for 18 h. The volatiles were evaporated in vacuo and the residue dissolved in dichloromethane (100 ml) and evaporated in vacuo. The residue was purified by column chromatography on silica gel (600 ml) using first a mixture of ethyl acetate/triethylamine 95:5 (1 l) followed by a mixture of ethyl acetate/methanol/triethylamine 90:5:5 as eluents affording 2.95 g of N-[[3-[N-(4-bromo-benzyl)-N-(pyridin-2-yl)amino]propylamino]-(4-pyridin-2-yl-piperazin-1-yl) methylene]benzamide as a foam.

Source