Morpholine → 4-(4-Bromo-3-methylbenzene-1-sulfonyl)morpholine

HRID 1644688Notes

Reaction equation

HRID 1644688 reaction equation
C(N(C(C)C)CC)(C)C.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.[Br:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][C:18]=1[CH3:27]>O1CCCC1>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)(=[O:25])=[O:24])=[CH:19][C:18]=1[CH3:27]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 27375034-Bromo-3-methylbenzene-1-sulfonyl chloride

Product 1

HCID 25615134-(4-Bromo-3-methylbenzene-1-sulfonyl)morpholine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diisopropylethylamine (8.25 mL, 46.4 mmol) was added at 0° C. to a stirred solution of morpholine (1.62 g, 18.5 mmol) in tetrahydrofuran (40 mL) and the reaction mixture was stirred at room temperature for 15 minutes. A 0.1 M solution of 4-bromo-3-methyl-benzenesulfonyl chloride (5.0 g, 19 mmol) in tetrahydrofuran was added at room temperature and the reaction mixture was stirred at room temperature for 2 hours. The solvent was evaporated off under reduced pressure. The residue was diluted with ethyl acetate, and the inorganic salts were filtered through a celite bed. The filtrate was washed with 2 N aqueous HCl, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford 4-(4-bromo-3-methyl-benzenesulfonyl)-morpholine, which was used in subsequent reactions without further purification. MS cald. for C11H14BrNO3S [M+] 320.2, obsd. 321.9.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 2 hours
  2. customThe solvent was evaporated off under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. filtrationthe inorganic salts were filtered through a celite bed
  5. washThe filtrate was washed with 2 N aqueous HCl
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d30db8cf16f84eb99fa5272d53a2fd14
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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