Water → 4-(4-Nitrobenzyl)morpholine

HRID 1387768Notes

Reaction equation

HRID 1387768 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].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.O>C1COCC1>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 660114-Nitrobenzyl bromide

Product 1

HCID 7831834-(4-Nitrobenzyl)morpholine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (250 ml) was dissolved 4-nitrobenzylbromide (25.0 g), and to the mixture was added morpholine (25.2 ml) at 0° C. The reaction mixture was stirred for 15 hours at room temperature. To the mixture was added water (500 ml), and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate) to give 4-(4-nitrobenzyl)morpholine (25.5 g) as pale yellow crystals. A portion of the crystals was recrystallized from dulsopropylether to give pale yellow crystals which were used for various analyses. mp 79-80° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified with column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-6e386b979bc841b38fde3093b004d7b2
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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