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

HRID 1181952Notes

Reaction equation

HRID 1181952 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-b2d0a976ad5b42b2bde7a3c2b3059fed
Source dataset
uspto-grants-2007_10
Patent number
US07285662B2

Reaction notes

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