Dimethylamine → 2-(6-Bromopyridin-3-yl)-N,N-dimethylethanamine

Participants

Reaction Conditions

Reaction Steps

2-(6-Bromopyridin-3-yl)ethanol (40 mg, 0.20 mmol) was dissolved in dichloroethane (3 ml), 200 mg of triethylamine was added to the solution, and the mixture was stirred at 4° C. under ice cooling. Mesyl chloride (68 mg, 0.60 mmol) was added to the reaction solution. After the dropwise addition, the mixture was stirred at 4° C. for 1 hr under ice cooling and was further stirred at room temperature for 30 min. The reaction solution was poured into 10 ml of iced water, was extracted with ml of ethyl acetate, and the extract was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under the reduced pressure. The residue was dissolved in DMF (2 ml), and the solution was stirred at room temperature. A 2 M solution (1 ml) of dimethylamine (2 mmol) in methanol was added thereto, and the mixture was stirred at 5.0° C. for 4 hr. The reaction solution was poured into 10 ml of iced water and was extracted with 20 ml of ethyl acetate. The extract was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under the reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:methanol=10:1) to give 12 mg (yield 28.1%) of the title compound.

Provenance & Evidence