Morpholine → 4-(6-Nitropyridin-3-yl)morpholine

HRID 1366205Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O.C(OCC)(=O)C>[N+:8]([C:5]1[N:6]=[CH:7][C:2]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-bromo-2-nitro-pyridine (5 g, 24.75 mmol), tetrabutyl ammonium iodide (0.46 g, 1.24 mmol), K2CO3 (3.76 g, 27.22 mmol) and morpholine (2.34 g, 27.22 mmol) in DMSO (50 mL) is stirred at 80° C. in a stem tube for 20 hours. The reaction mixture is diluted with ethyl acetate and filtered. The organic solution is washed with water, dried over MgSO4 and concentrated in vacuo. The residue is triturated with dichloromethane and hexane to afford the title compound as a solid (2.39 g, 46%).

Workup

filtrationfiltered
washThe organic solution is washed with water
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue is triturated with dichloromethane and hexane

Sources & evidence

ORD record: ord-0f95cd78dc7a411386897dd475e77728
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893058B2

Reaction notes

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