Réaction #75612

Équation de réaction

diethyl azodicarboxylate

1-(4-hydroxypiperidino)-4-(3-chloro-4-methoxybenzyl)amino-6-cyanophthalazine

phthalimide

triphenylphosphine

→

4-(3-chloro-4-methoxybenzyl)amino-6-cyano-1-(4-phthalimidopiperidino)phthalazine

Rendement 88.5%

Solvants

tetrahydrofuran

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Températurecooling
2. 2
   AutreThe reaction solution was evaporated
3. 3
   workup.ADDITIONwater and ethyl acetate were added
4. 4
   Autrethe insoluble matters were removed by filtration
5. 5
   ConcentrationThe organic layer was concentrated
6. 6
   Autrethe resulting residue was purified by silica gel column chromatography

Mode opératoire

Then, 30 ml solution of 3.48 g diethyl azodicarboxylate in tetrahydrofuran was added to 100 ml solution of 4.2 g 1-(4-hydroxypiperidino)-4-(3-chloro-4-methoxybenzyl)amino-6-cyanophthalazine, 2.94 g phthalimide, and 5.24 g triphenylphosphine in tetrahydrofuran over 30 min under ice-cooling, and then it was stirred at 4° C. for 24 hr. The reaction solution was evaporated, water and ethyl acetate were added thereto, and then the insoluble matters were removed by filtration. The organic layer was concentrated, and the resulting residue was purified by silica gel column chromatography to give 4.85 g of 4-(3-chloro-4-methoxybenzyl)amino-6-cyano-1-(4-phthalimidopiperidino)phthalazine.

Source