Trifluoroacetic acid → 1-(Methylsulfonyl)piperazine

Participants

Reaction Steps

N-tert-butoxycarbonyl-N'-methylsulfonylpiperazine (3.84 g, 14.5 mmol) was suspended in methylene chloride (100 mL) under nitrogen and trifluoroacetic acid (10 mL) was added. After 3 hours, the reaction mixture was concentrated in vacuo and the residue dissolved in water (150 mL). The aqueous layer was washed with ether (2×75 mL). The pH of the aqueous layer was then adjusted to 10 and it was extracted with methylene chloride (3×120 mL). The methylene chloride layers were dried over magnesium sulfate, and concentrated in vacuo to give 0.99 g of N-methylsulfonylpiperazine. Further extraction of the aqueous layer with 10% methanol/methylene chloride (3×120 mL) afforded 0.44 g of N-methylsulfonylpiperazine, for a total of 1.43 g (59%).

Provenance & Evidence