Morpholine → 1-(4-Biphenylyl)-2-(4-morpholinyl)ethanone

HRID 2114378Notes

Reaction equation

HRID 2114378 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:7]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]([C:13](=[O:16])[CH2:14]Br)=[CH:9][CH:8]=1>CCOCC.ClCCl>[C:7]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:8]=[CH:9][C:10]([C:13](=[O:16])[CH2:14][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 672821-(1,1'-Biphenyl)-4-yl-2-bromoethanone

Product 1

HCID 574186611-(4-Biphenylyl)-2-(4-morpholinyl)ethanoneYield 100.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of morpholine (5.99 g, 68.7 mmol) in ether (20 mL) was added the solution of 1-(4-biphenylyl)-2-bromoethanone (9.47 g, 34.4 mmol) in a mixture of ether (100 mL) and dichloromethane (100 mL) dropwise at 0° C. After the addition was over, the reaction mixture was allowed to warm to room temperature and stirred at room temperature for 1 h. The mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane (150 mL) and extracted with 5% NaHCO3 (150 mL) and brine (100 mL). The organic layer was dried (MgSO4) and concentrated to give 9.70 g (100%) of the title compound as a white solid. MS (ES) m/e 281.2 [M+H]+.

Workup

  1. additionAfter the addition
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane (150 mL)
  4. extractionextracted with 5% NaHCO3 (150 mL) and brine (100 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0b25ce01ce7f41679bc3fa099df4404f
Source dataset
uspto-grants-2008_10
Patent number
US07432258B2

Reaction notes

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