Reacción #5841

Ecuación de reacción

amorphous compound

N-[2-(4-Chloro-N-Methylcinnamylamino)ethyl]-5-Isoquinolinesulfonamide

1-piperidinethanol

triphenylphosphine

diethyl azodicarboxylate

→

title compound

Rendimiento 74.9%

N-[2-(4-Chloro-N-Methylcinnamylamino)Ethyl]-N-(2-Piperidinoethyl)-5-Isoquinolinesulfonamide

Rendimiento 74.9%

Disolventes

tetrahydrofuran

tetrahydrofuran

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was stirred for 2 hours
2. 2
   Otroevaporated
3. 3
   Otroto remove the solvent under a reduced pressure
4. 4
   Otroresulting residue
5. 5
   Extracciónextracted three times with 10 ml of 1N hydrochloric acid
6. 6
   Extracciónextracted three times with 10 ml of ehtyl acetate
7. 7
   Extracciónthe organic extract
8. 8
   Secadowas dried over magnesium sulfate
9. 9
   Otroevaporated
10. 10
    Otroto remove the solvent at a reduced pressure
11. 11
    Lavadoeluted with 2% methanol in chloroform

Procedimiento

To a solution of 0.39 g of the amorphous compound obtained in Example 190, 0.145 g of 1-piperidinethanol and 0.369 g of triphenylphosphine in 5 ml of tetrahydrofuran, was added dropwise a solution of 0.245 g of diethyl azodicarboxylate in 2 ml of tetrahydrofuran with stirring under ice cooling. The mixture was stirred for 2 hours and evaporated to remove the solvent under a reduced pressure, and resulting residue dissolved in 30 ml of ethyl acetate and extracted three times with 10 ml of 1N hydrochloric acid. The aqueous layer was alkallized with sodium bicarbonate and extracted three times with 10 ml of ehtyl acetate, and the organic extract was dried over magnesium sulfate and evaporated to remove the solvent at a reduced pressure. The resulting residue was applied to a silica gel column and eluted with 2% methanol in chloroform, to obtain 0.37 g of the title compound as a colorless oil.

Fuente