Piperazine → tert-Butyl 3-(piperazin-1-yl)azetidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Piperazine (23.69 g, 8 mol equivalent) was melted and 1-(t-butoxycarbonyl)-3-methanesulphonyloxyazetidine (see International Patent Application Publication no WO93/19059; 8.64 g, 34.4 mmol) added. The mixture was heated at 120° C. for 15 hours under nitrogen. The reaction was cooled to room temperature and the excess piperazine removed under reduced pressure. The residue was chromatographed on silica gel using gradient elution (methanol:dichloromethane 1:19 changing to 1:4, by volume) to give the title compound (6.32 g). LRMS m/z=242 (m+1)+. 1H-NMR (d6 -DMSO): δ=1.35(s,9H), 2.4-2.5(m,4H), 3.0-3.1 (m,5H), 3.2-4.2(m,br.,5H)ppm.

Provenance & Evidence