Morpholine → 4-((4-(Bromomethyl)phenyl)sulfonyl)morpholine

HRID 2266597Notes

Reaction equation

HRID 2266597 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(N(CC)CC)C>C(OCC)C.O>[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 27344094-(Bromomethyl)benzenesulfonyl chloride

Product 1

HCID 27796804-((4-(Bromomethyl)phenyl)sulfonyl)morpholine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 4-bromomethylbenzenesulfonyl chloride (0.81 g) in anhydrous diethyl ether (5.0 mL) at −10° C. was treated with a solution of morpholine (0.26 mL) and triethylamine (0.46 mL) in anhydrous diethyl ether (5.0 mL). The resulting mixture was warmed to room temperature over 1 hour and then stirred at this temperature for 17 hours. The mixture was diluted with water, extracted with dichloromethane and the combined extracts washed with saturated aqueous sodium chloride solution and then dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate and cyclohexane (3:7 by volume) to afford title compound, 0.53 g.

Workup

  1. extractionextracted with dichloromethane
  2. washthe combined extracts washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue purified by column chromatography on silica gel
  6. washeluting with a mixture of ethyl acetate and cyclohexane (3:7 by volume)

Sources & evidence

ORD record
ord-0737c60e4f9b4795beb1d28b07ced344
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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