Morpholine → 4-((3-Bromophenyl)sulphonyl)morpholine

HRID 1817615Notes

Reaction equation

HRID 1817615 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Br:7][C:8]1[CH:9]=[C:10]([S:14](Cl)(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=1>C1COCC1>[Br:7][C:8]1[CH:9]=[C:10]([S:14]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 17943m-Bromobenzenesulphonyl chloride

Product 1

HCID 36960024-((3-Bromophenyl)sulphonyl)morpholine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Morpholine (0.19 mL, 0.0022 mol) in 1.0 ml of THF was added dropwise to a solution of 3-bromobenzenesulfonyl chloride (0.3 mL, 0.002 mol) and TEA (0.30 mL, 0.0022 mol) in dry 4.0 mL of THF cooled in an ice bath. The reaction mixture was stirred overnight at room temperature and was then partitioned between 0.05N HCl and ethyl acetate. The organic layer was washed with water (2×), and brine (1×), and was then dried over anhydrous magnesium sulfate, filtered and then was concentrated in vacuo to give 4-[(3-bromophenyl)sulfonyl]morpholine as a white crystalline product (470 g, 78%). LCMS (M+H)+: m/z=306, 308.

Workup

  1. temperaturecooled in an ice bath
  2. customwas then partitioned between 0.05N HCl and ethyl acetate
  3. washThe organic layer was washed with water (2×), and brine (1×)
  4. dry with materialwas then dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-028f262e3e02448cba33447df7e2eea9
Source dataset
uspto-grants-2009_10
Patent number
US07598257B2

Reaction notes

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