Réaction #5686

Équation de réaction

hydrochloric acid

5-[2-(p-toluenesulfonyloxy)ethyl]-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

sodium iodide

4-acetylpiperazine

→

5-[2-(4-acetyl-1-piperazinyl)ethyl]-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine hydrochloride

Rendement 121.5%

Solvants

diethyl ether

dimethylformamide

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture is heated at 50° C. for 2 hours
2. 2
   workup.WAITfurther at 60° C. for 3 hours
3. 3
   Autrethe aqueous layer is collected
4. 4
   Extractionextracted with dichloromethane
5. 5
   LavageThe dichloromethane layer is washed with water
6. 6
   Autredried
7. 7
   workup.DISTILLATIONthe solvent is distilled off
8. 8
   workup.ADDITIONTo the resulting residue is added hydrochloric acid/ethanol

Mode opératoire

To a solution of 5-[2-(p-toluenesulfonyloxy)ethyl]-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.25 g) in dry dimethylformamide (20 ml) are added sodium iodide (0.178 g) and 4-acetylpiperazine (0.152 g), and the mixture is stirred at room temperature for one hour. The mixture is heated at 50° C. for 2 hours, and further at 60° C. for 3 hours. To the reaction solution are added 1N-hydrochloric acid and diethyl ether, and the aqueous layer is collected and neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with dichloromethane. The dichloromethane layer is washed with water, dried, and the solvent is distilled off. To the resulting residue is added hydrochloric acid/ethanol to give 5-[2-(4-acetyl-1-piperazinyl)ethyl]-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine hydrochloride (150 mg) as colorless amorphous.

Source