Hydrochloric Acid → 4-methylpiperazine-1-sulfonyl Chloride

To a solution of N-methylpiperazine (1.48 mL, 13.3 mmol) in dioxane (6.7 mL) cooled to 0° C. was added 4N hydrochloric acid in dioxane (10 mL). The reaction was very exothermic, and the mixture was stirred until the reaction cooled to room temperature. The solvent was removed under reduced pressure and chased with ether (2×). The solid obtained was taken up in acetonitrile (7 mL) and sulfuryl chloride (3.53 mL, 3.3 equiv) was added. The mixture was warmed at relux for 24 hours and the product removed by filtration and washed with 1:1 acetonitrile/ether (100 mL). This crude material was recrystallized from hot methanol and acetonitrile to afford 4-methylpiperazin-1-ylsulfonyl chloride (1.36 g, 44%) as a white crystalline solid.

1. customThe solvent was removed under reduced pressure and chased with ether (2×)
2. customThe solid obtained
3. temperatureThe mixture was warmed at relux for 24 hours
4. customthe product removed by filtration
5. washwashed with 1:1 acetonitrile/ether (100 mL)
6. customThis crude material was recrystallized from hot methanol and acetonitrile

ORD record

ord-dab81cd1872d437098be12ad89207e9b

Source dataset

uspto-grants-1994_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05338726