Trifluoroacetic acid → HCID 22498402, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 1-piperazinecarboxylate (2.5 g. 13.42 mmol) in tetrahydrofuran (21.5 ml, 0.25 M) at 0° C. was added triethylamine (2.25 mL, 16.11 mmol) followed by dimethylsulfamoyl chloride (1.73 mL, 16.11 mmol). The reaction mixture was stirred at 0° C. for 1 h, diluted with ethyl acetate (100 mL) and washed with saturated NaHCO3 solution (2×30 mL), followed by brine (2×30 mL). The dried (Na2SO4) organic layer was evaporated to dryness under reduced pressure and the residue obtained was treated with 10% trifluoroacetic acid in methylene chloride (20 mL) at ambient temperature. After 48 h, methylene chloride was evaporated in vacuo to obtain a colorless syrup. This crude material was made basic (1 N NaOH, 50 mL), and the mixture was extracted sequentially with ethyl acetate (2×20 mL) and methylene chloride (2×30 mL). The combined organic layers were dried (Na2SO4) and evaporated to dryness under reduced pressure to obtain the title compound in quantitative yield. 1H NMR (300 MHz, DMSO-d6) δ 2.77 (s, 3H), 2.79 (s, 3H), 3.12-3.20 (m, 7H), 3.3 (m, 1H), 8.86 (br s, 1H); MS (ESI) m/e 194 (M+H)+.

Provenance & Evidence