Bis(2-chloroethyl) ether → HCID 10754897, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of sodium hydride (0.70 g, 0.023 mol, 80% oil dispersion) and diphenylamine (3.4 g, 0.020 mol) in dry dibutylether (30 ml) was heated at reflux temperature for 1 h under an atmosphere of nitrogen. The reaction mixture was cooled to 50° C. and 2,2'-dichlorodiethylether (10 ml) was added and the mixture was heated at reflux temperature for 16 h. The reaction mixture was cooled, filtered and the volatile components were removed in vacuo leaving 4.6 g of crude 2-chloro-1-(2-(diphenylamino)ethoxy)ethane as an oil. This oil was dissolved in dry dibutylether (10 ml) and ethyl (R)-3-piperidinecarboxylate (3.7 g, 0.024 mol) and potassium carbonate (3.3 g, 0.024 mol) were added. The mixture was heated at reflux temperature for 2 h under an atmosphere of nitrogen and then stirred overnight at room temperature. Ethyl acetate (50 ml) was added, the mixture was filtered and the solvent was evaporated in vacuo. The residue was submitted to flash chromatography on silica gel (150 g) using a mixture of n-heptane and THF (4:1) as eluent. This provided 3.8 g (48% calculated from diphenylamine) of the title compound as an oil. TLC: rf=0.22 (SiO2 ; n-heptane/THF=7:3).

Provenance & Evidence