Reaktion #5840

Reaktionsgleichung

sodium cyanoborohydride

product

N-[2-(4-Chlorocinnamylamino)ethyl]-5-Isoquinolinesulfonamide

p-hydroxybenzaldehyde

→

title compound

Ausbeute 59.3%

N-{2-[4-Chloro-N-(4-Hydroxybenzyl)Cinnamylamino]ethyl}-5-Isoquinolinesulfonamide

Ausbeute 59.3%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated under a reduced pressure
2. 2
   workup.ADDITIONafter adding a saturated sodium chloride aqueous solution
3. 3
   Extraktionextracted three times with 20 ml of ethyl acetate
4. 4
   Waschenwashed with sodium chloride
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under a reduced pressure
8. 8
   SonstigeThe resulting residue was purified on a silica gel column (silica gel 10 g, eluant: 2% methanol in chloroform)

Vorschrift

0.2 g of the product of Example 172 and 0.13 g of p-hydroxybenzaldehyde were dissolved in 10 ml of methanol, to the solution were added 60 mg of sodium cyanoborohydride and two drops of acetic acid, and the mixture was stirred for 2 days at a room temperature. The reaction mixture was concentrated under a reduced pressure, and after adding a saturated sodium chloride aqueous solution, extracted three times with 20 ml of ethyl acetate. The extracts were combined, washed with sodium chloride, dried over magnesium sulfate, filtered and concentrated under a reduced pressure. The resulting residue was purified on a silica gel column (silica gel 10 g, eluant: 2% methanol in chloroform), to obtain 150 mg of the title compound in a colorless amorphous form.

Quelle