Reaktion #4414

Reaktionsgleichung

CH2Cl2 CH3OH ammonium hydroxide

1-(3-chlorobenzyl)piperazine

1-bromo-3-chloropropane

Hydrogen chloride

→

1,3-bis[4-(3-chlorobenzyl)-1-piperazinyl]propane dihydrochloride monohydrate

Ausbeute 68.0%

Lösungsmittel

ethanol

Water

ethanol

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 4 hours
2. 2
   Einengenthe mixture was concentrated under vacuum to about 70 ml
3. 3
   ExtraktionThe resulting aqueous mixture was extracted with ether (3×150 ml)
4. 4
   Einengenthe extract was concentrated under vacuum
5. 5
   Sonstigeto give a reddish-yellow oil
6. 6
   Sonstigeresulted in an oil which
7. 7
   FiltrationThe resulting precipitate was filtered off
8. 8
   Sonstigedried

Vorschrift

A mixture of 6.3 g of 1-(3-chlorobenzyl)piperazine, 2.4 g of 1-bromo-3-chloropropane, 50 ml of reagent ethanol and 3.0 g of triethylamine was refluxed for 4 hours. Water (70 ml) was added, and the mixture was concentrated under vacuum to about 70 ml. The resulting aqueous mixture was extracted with ether (3×150 ml), and the extract was concentrated under vacuum to give a reddish-yellow oil. Chromatography of this oil on a silica column, the eluant being CH2Cl2 /CH3OH/ammonium hydroxide (45:5:1), resulted in an oil which was dissolved in 50 ml of ethanol. Hydrogen chloride-saturated ether was added to this solution until the mixture tested acidic to litmus. The resulting precipitate was filtered off, dried and weighed to yield 5.6 g (68% of theory) of 1,3-bis[4-(3-chlorobenzyl)-1-piperazinyl]propane dihydrochloride monohydrate. Recrystallization from water gave a white crystalline solid (m.p. 248°-257° C., with decomp.).

Quelle