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

HRID 2080554Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][CH2:10][CH2:11][OH:12])=[CH:4][CH:3]=1.[CH3:13][O:14][CH2:15][CH2:16]Br.C(N(C(C)C)CC)(C)C>O1CCOCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:16][CH2:15][O:14][CH3:13])[CH2:10][CH2:11][OH:12])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 95 °C

Procedure

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.

Workup

temperatureAfter this time the reaction mixture was cooled to ambient temperature
concentrationwas concentrated under reduced pressure to a residue
customThe residue was purified by column chromatography on silica gel
washeluting with a mixture of methanol and methylene chloride
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-acc1230874244ab1b23aee7e5df306e5
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932393B2

Reaction notes

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