Ethyl Acetate → 4-(3-(4-Bromophenoxy)propyl)morpholin-3-one

HRID 1054694Notes

Reaction equation

HRID 1054694 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH2:11]Br)=[CH:4][CH:3]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][C:14]1=[O:19].[H-].[Na+].C(OCC)(=O)C>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH2:11][N:13]2[CH2:18][CH2:17][O:16][CH2:15][C:14]2=[O:19])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 669533-MorpholinoneHCID 3479241-Bromo-4-(3-bromopropoxy)benzene

Product 1

HCID 866986924-(3-(4-Bromophenoxy)propyl)morpholin-3-oneYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of 1-bromo-4-(3-bromopropoxy)benzene (300 mg, 1.02 mmol) and morpholin-3-one (100 mg, 1.02 mmol) in DMF (6 mL) was added NaH (365 mg, 1.10 mmol). The mixture was stirred at 75° C. for 5 hours. The mixture was poured into ethyl acetate and washed with water. The organic phase was dried over sodium sulfate, filtered, and concentrated to give the title compound (100 mg, 35%) as a yellow oil.

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d6e18605470f4735813e7f9723602d23
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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