1-(2-Hydroxyethyl)piperazine → VK-28

HRID 23940Notes

Reaction equation

HRID 23940 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.Cl[CH2:11][C:12]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]2[C:13]=1[CH:14]=[CH:15][CH:16]=[N:17]2>C(Cl)(Cl)Cl>[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:11][C:12]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]3[C:13]=2[CH:14]=[CH:15][CH:16]=[N:17]3)[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 4168815-(Chloromethyl)quinolin-8-ol

Product 1

HCID 4490594VK-28Yield 60%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

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.

Workup

  1. washThe reaction mixture was subsequently washed with a saturated NaHCO3 solution and brine
  2. dry with materialdried with Na2SO4
  3. customevaporated to dryness
  4. customCrystallization of the residue
  5. additionfrom a mixture of CHCl3-Hex

Sources & evidence

ORD record
ord-6d7a977f570e469b915f9acf0a785d69
Source dataset
uspto-grants-2005_02
Patent number
US06855711B1

Reaction notes

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