Réaction #4270

Équation de réaction

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

paraformaldehyde

piperidine

→

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

Solvants

dioxan

Conditions de réaction

Traitement

1. 1
   Températureis refluxed for 1 hour
2. 2
   Filtrationare filtered off
3. 3
   Autrethe filtrate is evaporated to dryness in vacuo
4. 4
   AutreThe crude product is purified by column chromatography on silica gel (mobile phase: ethyl acetate, ethyl acetate+10% methanol)
5. 5
   AutreAfter recrystallisation from ethyl acetate, 2.7 g (21% of theory) of the desired compound
6. 6
   Autreare obtained

Mode opératoire

A mixture consisting of 9.6 g (0.03 mol) of 5,11-dihydro-11-[1-oxo-4-pentynyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, 1.08 g (0.036 mol) of paraformaldehyde, 3.06 g (0.036 mol) of piperidine, 0.2 g of copper(I) chloride and 150 ml of dioxan is refluxed for 1 hour. After the reaction has ended the insoluble constituents are filtered off and the filtrate is evaporated to dryness in vacuo. The crude product is purified by column chromatography on silica gel (mobile phase: ethyl acetate, ethyl acetate+10% methanol). After recrystallisation from ethyl acetate, 2.7 g (21% of theory) of the desired compound are obtained, m.p. 197° C.

Source