Reaction #5838

Reaction equation

ethyl acetate

1,2-dibromoethane

potassium carbonate

product

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

→

title compound

Yield 25.5%

1-(4-Chlorocinnamyl)-4-(5-Isoquinolinesulfonyl)Piperazine

Yield 25.5%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   Washthe ethyl acetate layer was sequentially washed with water
2. 2
   Dryinga saturated sodium chloride aqueous solution twice in each case, and dried over magnesium sulfate
3. 3
   FiltrationThe solution was filtered
4. 4
   Otherevaporated under a reduced pressure
5. 5
   Otherresulting residue
6. 6
   Otherwas purified on a silica gel column (silica gel 50 g, eluant: 5% methanol in chloroform)

Procedure

1.31 g of the product of Example 172 was dissolved in 3 ml of dimethylformamide, to the solution were added 644 mg of 1,2-dibromoethane and 1.13 g of anhydrous potassium carbonate at a room temperature, and the mixture was stirred for 24 hours. After adding 100 ml of ethyl acetate, the ethyl acetate layer was sequentially washed with water and a saturated sodium chloride aqueous solution twice in each case, and dried over magnesium sulfate. The solution was filtered and evaporated under a reduced pressure, and resulting residue was purified on a silica gel column (silica gel 50 g, eluant: 5% methanol in chloroform), to obtain 356 mg of the title compound in a colorless amorphous form, while recovering the residual starting material.

Source