Sodium Hydroxide → (3S)-3-methyl-1-({4-[(trifluoromethyl)oxy]phenyl}sulfonyl)piperazine

Participants

Reaction Steps

A mixture of (2S)-2-methylpiperazine (1 g, 9.98 mmol, supplier Aldrich) in tetrahydrofuran (8 mL) and 3M aqueous sodium hydroxide (6.66 mL, 19.97 mmol) was cooled to 0° C. before addition of 4-[(trifluoromethyl)oxy]benzenesulfonyl chloride (2.86 g, 10.98 mmol, supplier Aldrich) dropwise via a dropping funnel. After addition, the cool bath was removed and the reaction stirred at room temperature for 4 h before standing at room temperature for 17 h. The mixture was concentrated in vacuo and then the residue was taken up in water (15 mL) and DCM (20 mL) and the mixture stirred for 1 h. The layers were separated and then the organic phase extracted with 1M HCl (40 mL). The acidic aqueous phase was then basified to pH12 with solid NaOH and the mixture extracted with DCM (2×30 mL). The combined organic phase was dried (phase separator) and concentrated under vacuum to give the title compound (2.58 g) as a colourless oil.

Provenance & Evidence