Morpholine → 4-(4-Bromobenzyl)morpholine

HRID 2421338Notes

Reaction equation

HRID 2421338 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>CN(C)C=O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 685274-Bromobenzyl bromide

Product 1

HCID 7835034-(4-Bromobenzyl)morpholine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromobenzyl bromide (2.0 g) and morpholine (1.39 ml) were stirred in dimethylformamide (25 ml) for 18 h. The mixture was partitioned between diethyl ether (50 ml) and water (80 ml). The aqueous phase was extracted further with ether (50 ml) and the combined organics were washed with water (80 ml), dried (magnesium sulphate) and evaporated. The residue was purified by column chromatography, eluting with a gradient of ethyl acetate/iso-hexane; 0/100 to 50/50, to give the product as a white crystalline solid (1.44 g).

Workup

  1. customThe mixture was partitioned between diethyl ether (50 ml) and water (80 ml)
  2. extractionThe aqueous phase was extracted further with ether (50 ml)
  3. washthe combined organics were washed with water (80 ml)
  4. dry with materialdried (magnesium sulphate)
  5. customevaporated
  6. customThe residue was purified by column chromatography
  7. washeluting with a gradient of ethyl acetate/iso-hexane

Sources & evidence

ORD record
ord-956fe342ac4640318f95055e203241be
Source dataset
uspto-grants-2011_06
Patent number
US07956084B2

Reaction notes

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