Reaktion #4271

Reaktionsgleichung

5,11-dihydro-11-[1-oxo-2-methyl-4-pentynyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

N-methylpiperazine

maleic acid

paraformaldehyde

→

5,11-Dihydro-11-[1-oxo-2-methyl-6-(4-methyl-1-piperazinyl)-4-hexynyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Lösungsmittel

water

dioxan

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturis refluxed for 2 hours
2. 2
   Filtrationis filtered over activated charcoal
3. 3
   Sonstigeto remove the insoluble components
4. 4
   Sonstigethe filtrate is evaporated to dryness in vacuo
5. 5
   SonstigeIn order to purify it
6. 6
   FiltrationThe insoluble matter is filtered off
7. 7
   workup.ADDITIONby the addition of potassium carbonate
8. 8
   Sonstigethe resin precipitated
9. 9
   TrocknenAfter drying over magnesium sulphate
10. 10
    Sonstigethe solution is evaporated to dryness in vacuo
11. 11
    Filtrationfiltered
12. 12
    Temperaturafter cooling
13. 13
    Sonstigeis obtained which melts at 212° to 214° C.
14. 14
    Waschenafter washing with ether

Vorschrift

A reaction mixture consisting of 36.6 g (0.12 mol) of 5,11-dihydro-11-[1-oxo-2-methyl-4-pentynyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, 4 g (0.13 mol) of paraformaldehyde, 13.2 g (0.13 mol) of N-methylpiperazine, 0.2 g of copper(I) chloride and 600 ml of dioxan is refluxed for 2 hours. After the reaction has ended the mixture is filtered over activated charcoal to remove the insoluble components and the filtrate is evaporated to dryness in vacuo. In order to purify it, the crude product is suspended in a solution of 15.4 g (0.13 mol) of maleic acid in 600 ml of water and stirred for 1 hour at ambient temperature. The insoluble matter is filtered off, the filtrate is made alkaline by the addition of potassium carbonate and the resin precipitated is taken up in 600 ml of methylene chloride. After drying over magnesium sulphate, the solution is evaporated to dryness in vacuo. The crystalline residue is decocted with 150 ml of ethyl acetate and suction filtered after cooling. By digesting it in a little ethyl acetate a crystalline product is obtained which melts at 212° to 214° C. after washing with ether.

Quelle