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

HRID 2421357Notes

Reaction equation

HRID 2421357 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-fc119b72487d40b4896374ba98a3b5fb
Source dataset
uspto-grants-2011_06
Patent number
US07956084B2

Reaction notes

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