Morpholine → 4-(4-Bromo-2-fluorobenzyl)morpholine

HRID 1245836Notes

Reaction equation

HRID 1245836 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[C:4]([F:10])[CH:3]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1>CN(C)C=O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[C:4]([F:10])[CH:3]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 27336604-Bromo-2-fluorobenzyl bromide

Product 1

HCID 219145034-(4-Bromo-2-fluorobenzyl)morpholine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromo-2-fluorobenzyl bromide (3.0 g) and morpholine (2.15 ml) were stirred in dimethylformamide (30 ml) at ambient temperature for 18 h. The mixture was partitioned between diethyl ether (80 ml) and water (80 ml). The aqueous phase was extracted further with diethyl ether (80 ml) and the combined organic phases were dried (magnesium sulfate) and concentrated in vacuo. The residue was purified by column chromatography, eluting with a gradient of 0–30% ethyl acetate/iso-hexane to give the product as a colourless oil (2.92 g).

Workup

  1. customThe mixture was partitioned between diethyl ether (80 ml) and water (80 ml)
  2. extractionThe aqueous phase was extracted further with diethyl ether (80 ml)
  3. dry with materialthe combined organic phases were dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography
  6. washeluting with a gradient of 0–30% ethyl acetate/iso-hexane

Sources & evidence

ORD record
ord-c8e00cdb47be467991686a50f45fdff7
Source dataset
uspto-grants-2006_10
Patent number
US07125896B2

Reaction notes

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