Morpholine → 1-(3-Bromophenyl)-2-(4-morpholinyl)ethanone

HRID 2114346Notes

Reaction equation

HRID 2114346 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Br[CH2:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Br:17])[CH:12]=1)=[O:10]>CCOCC.ClCCl>[Br:17][C:13]1[CH:12]=[C:11]([C:9](=[O:10])[CH2:8][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 5195852-Bromo-1-(3-bromophenyl)ethan-1-one

Product 1

HCID 208237461-(3-Bromophenyl)-2-(4-morpholinyl)ethanoneYield 101.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of morpholine (4.72 mL, 54.0 mmol) in ether (40 mL) cooled at 0° C., was added dropwise 2-bromo-1-(3-bromophenyl)ethanone (7.53 g, 27.0 mmol) in a mixture of ether (100 mL) and dichloromethane (100 mL). The reaction mixture was then warmed to room temperature, stirred at room temperature for 1 h, and concentrated under reduced pressure to give white solid. The white solid was dissolved in dichloromethane (200 mL) and washed with 5% NaHCO3 (200 mL) and brine (200 mL). The organic layer was dried (MgSO4) and concentrated to yield 1-(3-bromophenyl)-2-(4-morpholinyl)ethanone 7.8 g (100%) as a white solid, which was used without purification. MS (ESI): 284.2 [M+H]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto give white solid
  3. washwashed with 5% NaHCO3 (200 mL) and brine (200 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bb74c8e5cc9d407ca1574dbcb59dbbc6
Source dataset
uspto-grants-2008_10
Patent number
US07432258B2

Reaction notes

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