Morpholine → 4-(4-Bromobenzoyl)morpholine

HRID 2390232Notes

Reaction equation

HRID 2390232 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 685154-Bromobenzoyl chloride

Product 1

HCID 5321484-(4-Bromobenzoyl)morpholine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A cooled (0° C.) solution of 4-bromobenzoyl chloride (250 mg; 1.14 mmol) in THF (5 ml) was treated with a 2 M solution of morpholine in THF (219 μl; 2.51 mmol). The reaction mixture was allowed to warm to RT and stirred for 2 days, diluted with EtOAc and washed with a saturated NH4Cl solution in water. The organic phase was dried over MgSO4, filtered and concentrated to dryness affording the title compound as a pink solid (307 mg, quantitative yield).

Workup

  1. washwashed with a saturated NH4Cl solution in water
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-4f959da256f14008877d17ff4e7f72b4
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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