Morpholine → 1-[4-(4-Morpholinylsulfonyl)phenyl]ethanone

HRID 33460

Reaction equation

HRID 33460 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CCN(CC)CC.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>C(Cl)Cl>[N:21]1([S:10]([C:7]2[CH:8]=[CH:9][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][CH:6]=2)(=[O:12])=[O:11])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 2664184-Acetylbenzenesulfonyl chloride

Product 1

HCID 7467651-[4-(4-Morpholinylsulfonyl)phenyl]ethanoneYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4-acetylbenzenesulfonyl chloride (5.5 g, 25 mmol) in CH2Cl2 (75 mL) and Et3N (2 equiv, 7.0 mL, 50 mmol) was added morpholine (1.5 equiv, 3.3 mL, 38 mmol) dropwise. The mixture was stirred at room temperature for 30 min. The mixture was then diluted with CH2Cl2 (100 mL) and washed with 5% HCl (2×50 mL), water (50 mL), and then brine (50 mL). The organic layer was dried (Na2SO4), filtered, and concentrated to afford crude 1-[4-(morpholine-4-sulfonyl)phenyl]ethanone (2) (4.78 g, 18 mmol, 71%): HPLC Retention Time; 5.82 min. (Method B) M+1, 270.0.

Workup

  1. washwashed with 5% HCl (2×50 mL), water (50 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-25d03b4d43714d18a3d3e914cf144e3d
Source dataset
uspto-grants-2008_09
Patent number
US07429599B2

Linked notes

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