Reaktion #5841

Reaktionsgleichung

amorphous compound

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

1-piperidinethanol

triphenylphosphine

diethyl azodicarboxylate

→

title compound

Ausbeute 74.9%

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

Ausbeute 74.9%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred for 2 hours
2. 2
   Sonstigeevaporated
3. 3
   Sonstigeto remove the solvent under a reduced pressure
4. 4
   Sonstigeresulting residue
5. 5
   Extraktionextracted three times with 10 ml of 1N hydrochloric acid
6. 6
   Extraktionextracted three times with 10 ml of ehtyl acetate
7. 7
   Extraktionthe organic extract
8. 8
   Trocknenwas dried over magnesium sulfate
9. 9
   Sonstigeevaporated
10. 10
    Sonstigeto remove the solvent at a reduced pressure
11. 11
    Wascheneluted with 2% methanol in chloroform

Vorschrift

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.

Quelle