Morpholine → 4-(5-Fluoro-2-methoxy-benzenesulfonyl)-morpholine

HRID 1971834Notes

Reaction equation

HRID 1971834 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[F:7][C:8]1[CH:9]=[CH:10][C:11]([O:18][CH3:19])=[C:12]([S:14](Cl)(=[O:16])=[O:15])[CH:13]=1>C(Cl)Cl>[F:7][C:8]1[CH:9]=[CH:10][C:11]([O:18][CH3:19])=[C:12]([S:14]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)(=[O:15])=[O:16])[CH:13]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 27834095-Fluoro-2-methoxybenzene-1-sulfonyl chloride

Product 1

HCID 8499944-(5-Fluoro-2-methoxy-benzenesulfonyl)-morpholineYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a mixture of morpholine (5.8 g, 66.9 mmol) and TEA (9.3 ml, 66.9 mol) in CH2Cl2 (20 ml) was added dropwise a solution of the product of example 82 (5.0 g, 22 mmol) in CH2Cl2 (10 ml) at 0° C. After stirring at room temperature for one hour, the mixture was diluted with CH2Cl2, washed with water, dried and concentrated under reduced pressure. The resulting residue was purified by column chromatography (PE/EA=10/1) to give the titled compound (5.53 g, yield 90.3%).

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by column chromatography (PE/EA=10/1)

Sources & evidence

ORD record
ord-6f71ad169f2446b982fba24e3d5a6ee6
Source dataset
uspto-grants-2013_04
Patent number
US08431581B2

Reaction notes

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