Triethylamine → HCID 67071626, compound

Participants

Reaction Steps

To a stirred solution of 1-Boc-4-(2-aminoethyl)-piperazine (1.26 g, 6.8 mmol, Aldrich) and triethylamine (1 mL) in tetrahydrofuran (10 mL), 3-chloro-propylsulfonyl chloride (0.68 mL, 6.94 mmol, Aldrich) was added slowly at room temperature. The mixture was stirred for 30 min at room temperature and the reaction was quenched with water. It was extracted with ethyl acetate and the extracts were combined and dried over anhydrous sodium sulfate. The solids were filtered off, and the filtrate was concentrated in vacuo to give 4-[2-(3-chloro-propane-1-sulfonylamino)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester. It was taken in tetrahydrofuran (20 mL), and cesium carbonate (500 mg) sodium iodide (80 mg) were added and the mixture was stirred at reflux overnight. The mixture was cooled to room temperature and poured into water. It was extracted with ethyl acetate (3×15 mL), and the extracts were combined and dried over anhydrous sodium sulfate. The solids were filtered off, and the filtrate was concentrated in vacuo to give 2.01 g of 4-[2-(1,1-dioxo-isothiazolidine-2-yl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester as a solid. LR-MS: 334 [(M+H)+]

Provenance & Evidence