Morpholine → 4-(4-Nitrobenzyl)morpholine

HRID 1067955Notes

Reaction equation

HRID 1067955 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.C(OCC)(=O)C>CC(C)=O.O>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromide

Product 1

HCID 7831834-(4-Nitrobenzyl)morpholine

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a flask containing 4-nitrobenzyl bromide (21.6 g) in dry acetone (100 mL) is added potassium carbonate (34.5 g) and morpholine (10 mL). The mixture is heated to reflux overnight under a drying tube. The reaction is partioned between ethyl acetate and water and separated. The basic aqueous layer is extracted with two additional portions of ethyl acetate. The combined organic layers are washed with brine, dried, and concentrated under reduced pressure to afford 21.3 g of the title compound as a solid.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux overnight under a drying tube
  3. customseparated
  4. extractionThe basic aqueous layer is extracted with two additional portions of ethyl acetate
  5. washThe combined organic layers are washed with brine
  6. customdried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-abfe2f8896284c9ba7d65dfd3a13f3f2
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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