Reacción #4270

Ecuación de reacción

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

Disolventes

dioxan

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente