N-Benzylnormechlorethamine → HCID 59509446, compound

Participants

Reaction Conditions

Reaction Steps

Potassium carbonate (79.22 g, 0.572 mol) and tetrabutylammonium bromide (6.16 g, 0.019 mol) are added to a solution of benzyl-bis-(2-chloroethyl)amine (47.5 g, 0.205 mol) and diethyl malonate (30.62 g, 0.191 mol) in N,N-dimethylformamide (450 mL). The reaction mixture is heated at 80° C. for 1.5 hours and then concentrated under reduced pressure. The residue is treated with demineralized water (200 mL) and the aqueous layer is extracted with ethyl acetate (3×100 mL). Combined organic layers are washed with brine (1×40 mL) and dried over sodium sulphate. Removal of solvent gives a viscous liquid which is purified by column chromatography (silica gel 230-400 mesh, n-hexane:ethyl acetate 80:20) to give 1-benzylpiperidine-4,4-dicarboxylic acid diethyl ester.

Provenance & Evidence