Potassium Permanganate → 4-(4-Bromophenyl)morpholin-3-one

HRID 1012700Notes

Reaction equation

HRID 1012700 reaction equation
[Mn]([O-])(=O)(=O)=[O:2].[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][C:15]2=[O:2])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 116228514-(4-Bromophenyl)morpholine

Product 1

HCID 179827074-(4-Bromophenyl)morpholin-3-one

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

1.41 g (6.20 mmol) of benzyltriethylammonium chloride and 0.98 g (6.20 mmol) of potassium permanganate are added to a solution of 500 mg (2.07 mmol) of 4-(4-bromophenyl)morpholine (Example 15A) in 10 ml of dichloromethane. After 5 h under reflux, the contents of the flask are concentrated in vacuo, and the residue is purified by preparative HPLC. The concentrated product is dried under high vacuum. 217 mg (35.7% of theory) of the title compound are obtained.

Workup

  1. temperatureAfter 5 h under reflux
  2. concentrationthe contents of the flask are concentrated in vacuo
  3. customthe residue is purified by preparative HPLC
  4. customThe concentrated product is dried under high vacuum

Sources & evidence

ORD record
ord-12f7e0d9f9b743febf3eb545270d3b1f
Source dataset
uspto-grants-2011_07
Patent number
US07977485B2

Reaction notes

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