2-Bromoethyl methyl ether → 2-{[(6-Chloro(3-pyridyl))methyl](2-methoxyethyl)amino}ethan-1-ol

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 6.0 grams (0.03 mole) of 2-{[(6-chloro(3-pyridyl))methyl]amino}ethan-1-ol (known compound), 4.6 grams (0.033 mole) of 2-bromoethyl methyl ether and 5.8 grams (0.045 mole) if diisopropylethylamine in 120 mL of 1,4-dioxane was heated at 95° C. for 36 hours. After this time the reaction mixture was cooled to ambient temperature and was concentrated under reduced pressure to a residue. The residue was purified by column chromatography on silica gel, eluting with a mixture of methanol and methylene chloride. The appropriate fractions were combined and concentrated under reduced pressure, yielding 4.3 grams of 2-{[(6-chloro(3-pyridyl))methyl](2-methoxyethyl)amino}ethan-1-ol as an oil. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence