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

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Reaction Steps

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.

Provenance & Evidence