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

HRID 1972098Notes

Reaction equation

HRID 1972098 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.C(N(CC)CC)C.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>ClCCl.Cl>[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]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)morpholine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of commercially-available 4-bromomethyl benzenesulfonyl chloride (1.0 g, 3.71 mmol) in dichloromethane (8 ml) at 0° C. under an argon atmosphere, is added triethylamine (0.575 ml, 4.1 mmol), in one portion, followed by morpholine (0.359 ml, 4.1 mmol). The reaction mixture is stirred for 20 h, warming up slowly to room temperature. The reaction mixture is then diluted with 2N HCl aq (40 ml) and extracted with dichloromethane (20 ml), dried (MgSO4) and evaporated to dryness in vacuo to afford the title compound. Used crude in next step.

Workup

  1. extractionextracted with dichloromethane (20 ml)
  2. dry with materialdried (MgSO4)
  3. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-b9cde844eb9f4063becf48732f1663ec
Source dataset
uspto-grants-2013_04
Patent number
US08431703B2

Reaction notes

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