Réaction #63614

Équation de réaction

1,1'-(5-chloropentylidene)bis(4-fluorobenzene)

3-(aminocarbonyl)-N-(2,6-dichlorophenyl)-1-piperazineacetamide

sodium carbonate

potassium iodide

→

3-(aminocarbonyl)-4-[4,4-bis(4-fluorophenyl)pentyl]-N-(2,6-dichlorophenyl)-1-piperazineacetamide dihydrochloride monohydrate

Solvants

4-methyl-2-pentanone

Conditions de réaction

Traitement

1. 1
   Températurerefluxed for 24 hours
2. 2
   TempératureThe reaction mixture was cooled
3. 3
   Autrepurified by column-chromatography (2x) over silica gel using first
4. 4
   workup.ADDITIONa mixture of trichloromethane and methanol (95:5 by volume)
5. 5
   workup.ADDITIONa mixture of trichloromethane and methanol (97:3 by volume) as eluents
6. 6
   AutreThe pure fractions were collected
7. 7
   Autrethe eluent was evaporated
8. 8
   workup.STIRRINGAfter stirring for one hour at room temperature
9. 9
   Filtrationthe salt was filtered off
10. 10
    Autredried

Mode opératoire

A mixture of 5 parts of 1,1'-(5-chloropentylidene)bis(4-fluorobenzene), 5 parts of 3-(aminocarbonyl)-N-(2,6-dichlorophenyl)-1-piperazineacetamide, 2.2 parts of sodium carbonate, 0.1 parts of potassium iodide and 120 parts of 4-methyl-2-pentanone was stirred and refluxed for 24 hours. The reaction mixture was cooled and purified by column-chromatography (2x) over silica gel using first a mixture of trichloromethane and methanol (95:5 by volume) and then a mixture of trichloromethane and methanol (97:3 by volume) as eluents. The pure fractions were collected and the eluent was evaporated. The residue was converted into the hydrochloride salt in acetonitrile and 2-propanol. After stirring for one hour at room temperature, the salt was filtered off and dried, yielding 1.53 parts of 3-(aminocarbonyl)-4-[4,4-bis(4-fluorophenyl)pentyl]-N-(2,6-dichlorophenyl)-1-piperazineacetamide dihydrochloride monohydrate; mp. 206.2° C. (compound 49).

Source