Morpholine → HCID 15851763, compound

HRID 1431781Notes

Reaction equation

HRID 1431781 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C(=O)([O-])[O-].[K+].[K+].[NH:54]1[CH2:59][CH2:58][O:57][CH2:56][CH2:55]1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)(C)(C)C>[N+:11]([C:4]1[CH:3]=[C:2]([N:54]2[CH2:59][CH2:58][O:57][CH2:56][CH2:55]2)[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=1)([O-:13])=[O:12]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 445341-Bromo-3,5-dinitrobenzeneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl

Product 1

HCID 15851763HCID 15851763, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6386tert-ButanolSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 1-bromo-3,5-dinitrobenzene (2.84 g, 11.50 mmol), XPhos (0.493 g, 1.035 mmol), palladium (II) acetate (0.077 g, 0.345 mmol), potassium carbonate (2.225 g, 16.10 mmol), tert-butanol (23.0 mL), and morpholine (1.20 mL, 13.80 mmol) was stirred at 95° C. under nitrogen for 3 h. Upon completion, the reaction was partitioned between EtOAc and water. The organic layer was dried over magnesium sulfate and concd, and the crude material was purified by column chromatography (silica; 0-25% EtOAc in hexanes) to afford 4-(3,5-dinitrophenyl)morpholine as an orange amorphous solid. Mass Spectrum (ESI) m/e=254.2 (M+1).

Workup

  1. customUpon completion, the reaction was partitioned between EtOAc and water
  2. dry with materialThe organic layer was dried over magnesium sulfate and concd
  3. customthe crude material was purified by column chromatography (silica; 0-25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9ba62a1b0dd946feadea4f3380e3c941
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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