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

HRID 1921832Notes

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-8a953f44ab9a43dfa427e1c31f197fb8
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173656B2

Reaction notes

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