Tert-Butyl hypochlorite → HCID 86642705, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(3-amino-3-methylbutyl)-1,4,4-trimethylpiperidinium chloride hydrochloride (0.50 g, 1.73 mmol) in a mixture of methanol (10 mL) and water (8 mL) was cooled in an ice bath for 15 min. t-BuOCl (0.62 mL, 3 equiv, 5.21 mmol) was added in one portion via syringe to the colorless solution to give a deep yellow solution. The reaction mixture was stirred for 30 min at 0° C., then concentrated under reduced pressure to yield a colorless oil. This oil was dissolved into water and purified via reverse phase chromatography on a Shimadzu Prep-LC utilizing water/acetonitrile and 0.05% acetic acid as modifier. Fractions were collected monitoring UV absorbance at 215 nm. Fractions were pooled and concentrated via rotovap with the water bath set at 25° C. to give a pale yellow foam, (0.373 g, 67.8%). 1H NMR (D2O, 400 MHz): δ 1.06 (s, 3H), 1.07 (s, 3H), 1.46 (s, 6H), 1.64-1.80 (m, 4H), 2.21-2.27 (m, 2H), 3.05 (s, 3 H), 3.35-3.45 (m, 6H). LRMS (ESI+) for C13H27Cl2N2+ (281.1); Found: 281, 283 (M+, M2H+).

Provenance & Evidence