Morpholine → 4-((4-Fluorophenyl)sulfonyl)morpholine

HRID 1715686Notes

Reaction equation

HRID 1715686 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 95884-Fluorobenzenesulfonyl chloride

Product 1

HCID 7553774-((4-Fluorophenyl)sulfonyl)morpholineYield 101.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-fluorobenzenesulfonyl chloride (3.97 g, 20 mmol) in methylene chloride (40 ml), at 0° C., under nitrogen, with stirring, is added morpholine (4.4 mL, 50 mmol). The mixture is stirred at 0° C. for 15 min. and then warmed to room temperature for 18 hrs. The resulting suspension is filtered, and the filtrate is stirred with 10% potassium carbonate for 2 hrs. The methylene chloride is evaporated, and the aqueous suspension is filtered, and the precipitate is washed with water, and then dried in vacuo to give 5.0 g of a white solid; mp 106-107° C.; MS (APCI) m/z 246.1 (M+H).

Workup

  1. temperaturewarmed to room temperature for 18 hrs
  2. filtrationThe resulting suspension is filtered
  3. stirringthe filtrate is stirred with 10% potassium carbonate for 2 hrs
  4. customThe methylene chloride is evaporated
  5. filtrationthe aqueous suspension is filtered
  6. washthe precipitate is washed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-1768598440c04d6c9a45741b549f4bdb
Source dataset
uspto-grants-2010_09
Patent number
US07799915B2

Reaction notes

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