Morpholine → (Morpholin-4-yl)(4-nitrophenyl)methanone

HRID 2414493Notes

Reaction equation

HRID 2414493 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(N(CC)CC)C.C(OCC)(=O)C>O1CCCC1>[N:13]1([C:8]([C:7]2[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[O:9])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 8857Ethyl Acetate

Product 1

HCID 220838(Morpholin-4-yl)(4-nitrophenyl)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Nitrobenzoyl chloride (5 g, 27 mmol) in tetrahydrofuran (10 mL) was added slowly to a solution of morpholine (5 g, 88 mmol) and triethylamine (2.7 g, 27 mmol) in tetrahydrofuran (50 mL), and stirred at room temperature for four hours. Ethyl acetate (200 mL) was added to the mixture and the combined mixture was washed with water (25 mL), 1N HCl (25 mL), water (25 mL), saturated sodium bicarbonate (25 mL), water (25 mL) and brine (25 mL). The mixture was dried (Na2SO4), filtered and concentrated under vacuum and the residue used without further purification.

Workup

  1. washthe combined mixture was washed with water (25 mL), 1N HCl (25 mL), water (25 mL), saturated sodium bicarbonate (25 mL), water (25 mL) and brine (25 mL)
  2. dry with materialThe mixture was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customthe residue used without further purification

Sources & evidence

ORD record
ord-af21e53914f84520a7ff65c36c7e3be3
Source dataset
uspto-grants-2004_11
Patent number
US06812225B2

Reaction notes

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