Reaction #52218

Reaction equation

4-(2-Hydroxyethyl)-piperazine

5-chloromethyl-8-hydroxyquinoline

→

title product

Yield 60.0%

5-(4-(2-hydroxyethyl)piperazin-1-ylmethyl)-8-hydroxyquinoline

Yield 60.0%

Solvents

CHCl3

Conditions

Workup

1. 1
   WashThe reaction mixture was subsequently washed with a saturated NaHCO3 solution and brine
2. 2
   Dryingdried with Na2SO4
3. 3
   Otherevaporated to dryness
4. 4
   OtherCrystallization of the residue
5. 5
   workup.ADDITIONfrom a mixture of CHCl3-Hex

Procedure

4-(2-Hydroxyethyl)-piperazine (7.2 ml; 58.7 mmol) was added to a suspension of 5-chloromethyl-8-hydroxyquinoline (5.413 g; 23.5 mmol) in CHCl3 (80 ml) at 0° C. The mixture was stirred overnight at room temperature. The reaction mixture was subsequently washed with a saturated NaHCO3 solution and brine, then dried with Na2SO4 and evaporated to dryness. Crystallization of the residue from a mixture of CHCl3-Hex gave 4.05 g (60%) of title product. M.p. 123-4° C. The mother liquor was evaporated and the residue was crystallized to yield 1.5 g of title product. Overall yield: 5.55 g (82%). A highly pure product was obtained by soxleth extraction using hexane as the extractant. TLC (CHCl3 MeOH NH3=8:2:0.5). Rf=0.4.

Source