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

HRID 244270Notes

Reaction equation

HRID 244270 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)morpholineYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 4-bromomethylbenzenesulfonyl chloride (1.62 g, 6.01 mmol) in anhydrous diethyl ether (10 mL) at −10° C. was added a solution of morpholine (0.52 mL, 5.94 mmol) and triethylamine (0.92 mL, 6.6 mmol) in anhydrous diethyl ether (10 mL). The resulting mixture was allowed to warm up to room temperature over 1 hr, and continue stirring at r.t. overnight. The reaction mixture was then diluted with water, extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with water, brine, dried over Na2SO4, and filtered. Solvents were removed to yield an orange oil, which was purified on a 40 g silica gel column to give a white solid (1.34 g, 71% yield). 1H NMR (CD2Cl2) δ ppm: 7.75 (d, J=8.4 Hz, 2H), 7.63 (d, J=8.4 Hz, 2H), 4.58 (s, 2H), 3.77-3.73 (m, 2H), 3.03-2.98 (m, 2H). MS (ESI+): 320 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (2×30 mL)
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customSolvents were removed
  6. customto yield an orange oil, which
  7. customwas purified on a 40 g silica gel column

Sources & evidence

ORD record
ord-13b4849bbc1a40dda980430c6255df12
Source dataset
uspto-grants-2014_02
Patent number
US08658129B2

Reaction notes

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