Sodium Sulfite → 4-(4-Nitrophenyl)-morpholin-3-ON

HRID 902189Notes

Reaction equation

HRID 902189 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[Mn]([O-])(=O)(=O)=[O:17].[K+].[O-]S([O-])=O.[Na+].[Na+]>C(Cl)Cl.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][C:11]2=[O:17])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 3

HCID 24437Sodium SulfiteHCID 252224-(4-Nitrophenyl)morpholineHCID 516875Potassium Permanganate

Product 1

HCID 114473754-(4-Nitrophenyl)-morpholin-3-ON

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 10 g 4-(4-Nitro-phenyl)-morpholine in 200 mL DCM, 32 g Benzyl-triethyl-ammonium chloride and 22.7 g potassium permanganate (325 mesh) were cautiously added at RT. After stirring for 1 h the reaction mixture was heated to reflux for 10 h. Then, a solution of 95 g Na2SO3 in 450 mL water was added under ice cooling and vigorous stirring. The mixture was filtered through a pad of celite and the filtrate was concentrated under reduced pressure. The yellow solid was stirred with 250 mL water and the precipitated product was collected by filtration. This crude product was purified by chromatography on silica gel eluting with a gradient of DCM/MeOH 100%->50%. The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 2.6 g.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 10 h
  3. filtrationThe mixture was filtered through a pad of celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. stirringThe yellow solid was stirred with 250 mL water
  6. filtrationthe precipitated product was collected by filtration
  7. customThis crude product was purified by chromatography on silica gel eluting with a gradient of DCM/MeOH 100%->50%
  8. additionThe fractions containing the product
  9. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-29f531499e4e4079a2a0caad3efffe27
Source dataset
uspto-grants-2008_04
Patent number
US07365088B2

Reaction notes

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