Methyl vinyl sulfone → 2,2-Dimethyl-1-(2-(methylsulfonyl)ethyl)piperazine

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,3-dimethylpiperazine-1-carboxylic acid tert-butyl ester (500 mg, 2.33 mmol) and methyl vinyl sulfone (510 μL, 619 mg, 5.83 mmol) in MeOH (15 mL) was heated to 65° C. for 5.5 h then stirred at room temperature for 96 h. The reaction mixture was concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, MeOH:DCM, 0-3%) affording 1-(2-(Methanesulfonyl)ethyl)-2,2-dimethylpiperazine as a white waxy solid (550 mg, 74%). 1H NMR (CDCl3, 300 MHz): δ 3.47-3.40 (m, 2 H); 3.15 (s, 2 H); 3.09 (t, J=6.4 Hz, 2 H); 3.03 (s, 3 H); 2.89 (t, J=6.4 Hz, 2 H); 2.58-2.50 (m, 2 H); 1.45 (s, 9 H); 1.04 (s, 6 H).

Provenance & Evidence