Reaction #52191

Reaction equation

water

2-[2-(4-Amidinophenyl)-ethyl]-1-methyl-benzimidazole-5-yl-carboxylic acid-(4-benzamido-piperidinyl)-amide

Triethylamine

benzoyl chloride

→

2-[2-(4-Benzoylamidinophenyl)-ethyl]-1-methyl-benzimidazole-5-yl-carboxylic acid-(4-benzamidopiperidinyl)-amide

Solvents

dimethyl formamide

Conditions

Workup

1. 1
   Extractionthe aqueous phase is extracted with 20 ml of acetic ester
2. 2
   WashThe organic phase is again washed with waterand
3. 3
   Dryingdried over sodium sulphate
4. 4
   workup.DISTILLATIONThe solvent is distilled off under vacuum
5. 5
   OtherThe residue is chromatographed over silica gel with acetic ester
6. 6
   Otherthe oily product is triturated with petroleum ether
7. 7
   FiltrationThe precipate is filtered
8. 8
   Washwashed with petroleum ether
9. 9
   Other150-154° C.

Procedure

1.0 g (2 mmol) of 2-[2-(4-Amidinophenyl)-ethyl]-1-methyl-benzimidazole-5-yl-carboxylic acid-(4-benzamido-piperidinyl)-amide and 3.2 ml Triethylamine (23 mmol) are dissolved in 10 ml of dimethyl formamide. The mixture is cooled down to 0° C. and 0.418 ml of benzoyl chloride (3.6 mmol) are slowly added dropwise. After 2 hours 20 ml of water are added to the mixture, and the aqueous phase is extracted with 20 ml of acetic ester. The organic phase is again washed with waterand dried over sodium sulphate. The solvent is distilled off under vacuum. The residue is chromatographed over silica gel with acetic ester, and the oily product is triturated with petroleum ether. The precipate is filtered and washed with petroleum ether. Yield: 0.160 g (15%); MPt: 150-154° C.;

Source