Réaction #4411

Équation de réaction

1-phenacylpiperazine

1-chloro-3-[4-(4-chlorobenzyl)-1-piperazinyl]propane

triethylamine

→

1-[4-(4-chlorobenzyl)-1-piperazinyl]-3-(4-phenacyl-1-piperazinyl)propane

Rendement 77.5%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   Températurewas refluxed for 5 hours
2. 2
   AutreThe solvent was removed by rotary evaporation, 150 ml of water
3. 3
   workup.ADDITIONwere added
4. 4
   Extractionthe mixture was extracted with ether (3×150 ml)
5. 5
   AutreThe ether solution was evaporated to an oil, which
6. 6
   Autrewas chromatographed on a silica column

Mode opératoire

A mixture of 4.1 g of 1-phenacylpiperazine, 5.7 g of 1-chloro-3-[4-(4-chlorobenzyl)-1-piperazinyl]propane, 2.6 g of triethylamine and 35 ml of reagent ethanol was refluxed for 5 hours. The solvent was removed by rotary evaporation, 150 ml of water were added, and the mixture was extracted with ether (3×150 ml). The ether solution was evaporated to an oil, which was chromatographed on a silica column, the eluant being CH2Cl2 /CH3OH/ammonium hydroxide (45:5:1), to yield crude 1-[4-(4-chlorobenzyl)-1-piperazinyl]-3-(4-phenacyl-1-piperazinyl)propane (7.0 g, 50% of theory). This oil was dissolved in 200 ml of ether and precipitated with excess anhydrous hydrogen chloride. The precipitate was then dissolved in water and reprecipitated by addition of acetone to give 1-[4-(4-chlorobenzyl)-1-piperazinyl]-3-(4-phenacyl-1-piperazinyl)propane tetrahydrochloride monohydrate as a white crystalline product (m.p. 211°-218° C.).

Source