1-Piperazinecarboxylic acid, ethyl ester → Ethyl 4-[(8-hydroxyquinolin-5-yl)methyl]piperazine-1-carboxylate

HRID 23941

Reaction equation

HRID 23941 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].Cl.Cl[CH2:14][C:15]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]2[C:16]=1[CH:17]=[CH:18][CH:19]=[N:20]2.C(N(C(C)C)CC)(C)C>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([CH2:14][C:15]2[CH:24]=[CH:23][C:22]([OH:25])=[C:21]3[C:16]=2[CH:17]=[CH:18][CH:19]=[N:20]3)[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 81531DiisopropylethylamineHCID 122695968-Quinolinol, 5-(chloromethyl)-, hydrochloride (1:1)

Product 1

HCID 1090305Ethyl 4-[(8-hydroxyquinolin-5-yl)methyl]piperazine-1-carboxylateYield 42.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

N-Ethoxycarbonylpiperazine (1.5 ml, 10.2 mmol) was added to a mixture of 5-chloromethyl-8-hydroxyquinoline hydrochloride (2.36 g, 10.2 mmol) and diisopropylethylamine (3.6 ml, 20.6 mmol) in CHCl3 (50 ml) at 5° C. The mixture was stirred for 24 h at room temperature. CHCl3 (100 ml) was then added and the solution was washed with 5% NaHCO3 (3×50 ml) and brine (2×50 ml) and then dried over Na2SO4. The solution was filtered and evaporated to dryness. The residue was crystallized from a mixture of benzene hexane and gave 1.38 g (42%) of the title product. M.p. −96° C. TLC (CHCl3-MeOH-NH3 9:1:0.1) Rf=0.6; TLC (CHCl3-MeOH-Me3 9:0.5:0.05) Rf−0.4.

Workup

  1. washthe solution was washed with 5% NaHCO3 (3×50 ml) and brine (2×50 ml)
  2. dry with materialdried over Na2SO4
  3. filtrationThe solution was filtered
  4. customevaporated to dryness
  5. customThe residue was crystallized from a mixture of benzene hexane

Sources & evidence

ORD record
ord-42f95f73faf44ca99a56964d76d6bf47
Source dataset
uspto-grants-2005_02
Patent number
US06855711B1

Linked notes

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