Reaction #487577

Reaction equation

1-(2-chloroethyl)-3-(1-(5-cyano-2-(3,5-dichlorophenoxy)-phenylsulfonyl)piperidin-4-yl)urea

potassium carbonate

morpholine

→

product

Yield 65.5%

1-(1-(5-cyano-2-(3,5-dichlorophenoxy)phenylsulfonyl)piperidin-4-yl)-3-(2-morpholinoethyl)urea

Yield 65.5%

Solvents

acetonitrile

acetone

Conditions

Workup

1. 1
   Temperatureheated to reflux
2. 2
   ConcentrationThe mixture was then concentrated in vacuo
3. 3
   Otherthe solid triturated with dichlormethane and isopropyl ether
4. 4
   Otherto obtain a white powder
5. 5
   Temperaturecooled in an ice bath
6. 6
   Filtrationfiltered
7. 7
   Washwashed with water

Procedure

1-(2-chloroethyl)-3-(1-(5-cyano-2-(3,5-dichlorophenoxy)-phenylsulfonyl)piperidin-4-yl)urea (838 mg), potassium carbonate (655 mg, 3.0 eq.) and morpholine (413 mg, 3.0 eq.) were dissolved in acetonitrile (25 mL) and heated to reflux. After three hours, the reaction was complete (confirmed by HPLC). The mixture was then concentrated in vacuo, the solid triturated with dichlormethane and isopropyl ether to obtain a white powder. The powder was suspended in hot acetone, cooled in an ice bath, filtered, and washed with water to obtain the product as a white powder (601 mg, 65% yield, 97% purity).

Source