3-Morpholinophenol → 4-(3-(2-Nitropyridin-3-yloxy)phenyl)morpholine

HRID 911891Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].F[C:25]1[C:26]([N+:31]([O-:33])=[O:32])=[N:27][CH:28]=[CH:29][CH:30]=1>C1COCC1>[N+:31]([C:26]1[C:25]([O:13][C:9]2[CH:8]=[C:7]([N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)[CH:12]=[CH:11][CH:10]=2)=[CH:30][CH:29]=[CH:28][N:27]=1)([O-:33])=[O:32]

Participants

Conditions

Temperature: 0 °C

Procedure

In a 125 mL round-bottom flask, 3-morpholinophenol (0.91 g, 5.07 mmol) was dissolved in THF (40 mL). Solution was cooled to 0° C. and NaHMDS (5.07 mL, 5.07 mmol) (1M in THF) was added slowly. The mixture was agitated for 15 minutes and solution of 3-fluoro-2-nitropyridine (0.60 g, 4.22 mmol) in THF (5 mL) was added slowly. After agitating for 2 hours the solvent was evaporated and the residue dissolved in 100 mL of CH2Cl2 and washed with diluted sodium bicarbonate solution twice, dried over magnesium sulfate, filtered and evaporated. Crude material was purified by chromatography on silica gel, eluted with 25% ethyl acetate/Hexane to give the title compound (0.93 g, 72%) was obtained as thick red oil.

Workup

stirringAfter agitating for 2 hours the solvent
customwas evaporated
dissolutionthe residue dissolved in 100 mL of CH2Cl2
washwashed with diluted sodium bicarbonate solution twice
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated
customCrude material was purified by chromatography on silica gel
washeluted with 25% ethyl acetate/Hexane

Sources & evidence

ORD record: ord-f0d574d30d8046b0963ca830742a6d30
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022223B2

Reaction notes

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