Triethylamine → HCID 10140787, compound

Participants

Reaction Conditions

Reaction Steps

To a 10 mL round-bottomed flask, in an ice bath, fitted with a thermometer, and under a nitrogen atmosphere, of (2-{4-[4-(2-aminoethyl)phenyl]phenoxy}propyl)[(methylethyl)sulfonyl]amine hydrochloride (150 mg, 0.3984 mmol, prepared in example 39) dissolved in methylene chloride (2.7 mL) was added triethylamine (0.07 mL, 0.478 mmol). Once the mixture was cooled to 0° C., 2-propanesulfonyl chloride (0.05 mL, 0.4382 mmol) was added by syringe, and the mixture was gradually warmed to room temperature, with stirring overnight. The reaction was quenched with excess water, and the organic layer was dried with anhydrous sodium sulfate, filtered, and concentrated under vacuum, yielding 265 mg viscous oil. Purification was conducted using a Chromatotron®, on a 4000 μm rotor and eluting with a 1:1 hexane:ethyl acetate solvent system, yielding the title compound (200 mg, 100%) as a slow crystallizing foam.

Provenance & Evidence