Réaction #2387353

Équation de réaction

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

hydrazine monohydrate

→

title compound

Rendement 30.4%

1-(4-Aminopiperidino)-4-(3-chloro-4-methoxybenzyl)amino-6-cyanophthalazine Dihydrochloride

Rendement 30.4%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   Températurewas heated
2. 2
   Températureunder reflux for 1 hr
3. 3
   AutreThe reaction solution was evaporated
4. 4
   workup.DISSOLUTIONdissolved in ethyl acetate
5. 5
   workup.ADDITION1 N hydrochloric acid was added
6. 6
   Autreto 3, and the insoluble matters were removed by filtration
7. 7
   Extractionextracted with ethyl acetate
8. 8
   LavageThe organic layer was washed with brine
9. 9
   Séchagedried over anhydrous sodium sulfate
10. 10
    Autreevaporated
11. 11
    Autrepurified by silica gel column chromatography
12. 12
    workup.ADDITION1 N aqueous hydrochloric acid was added
13. 13
    workup.DISSOLUTIONdissolved
14. 14
    Températureby heating
15. 15
    TempératureAfter cooling
16. 16
    Filtrationthe resulting crystals were collected by filtration

Mode opératoire

A mixture of 4.85 g of the resulting 4-(3-chloro-4-methoxybenzyl)amino-6-cyano-1-(4-phthalimidopiperidino)phthalazine, 4 ml hydrazine monohydrate and 40 ml ethanol was heated under reflux for 1 hr. The reaction solution was evaporated, dissolved in ethyl acetate, and 1 N hydrochloric acid was added thereto to adjust the pH thereof to 3, and the insoluble matters were removed by filtration. The aqueous layer in the filtrate was adjusted to pH 11 with 1 N sodium hydroxide, and then extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, evaporated, and then purified by silica gel column chromatography. The resulting product was suspended in ethanol/water, then 1 N aqueous hydrochloric acid was added thereto and dissolved by heating. After cooling, the resulting crystals were collected by filtration to give 440 mg of the title compound as a yellow powder.

Source