Melatonin → Melatonin Impurity 3

HRID 370057

Reaction equation

HRID 370057 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][C:9]([NH:11][CH2:12][CH2:13][C:14]1[C:18]2[CH:19]=[C:20]([O:23][CH3:24])[CH:21]=[CH:22][C:17]=2[NH:16][CH:15]=1)=[O:10]>C1C=CC=CC=1>[CH3:24][O:23][C:20]1[CH:19]=[C:18]2[C:17](=[CH:22][CH:21]=1)[NH:16][CH:15]=[C:14]2[CH2:13][CH2:12][N:11]([C:1]([CH3:2])=[O:3])[C:9](=[O:10])[CH3:8]

Participants

4

Reactant 2

HCID 896MelatoninHCID 7918Acetic Anhydride

Product 1

HCID 832313Melatonin Impurity 3Yield 50%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Acetic anhydride (7 ml) is added with stirring to melatonin (500 mg) dissolved in benzene (50 ml). The mixture is heated for 72 h in refluxing benzene. The solvent is evaporated off and the crude product is taken up in water and then neutralized with sodium carbonate solution (pH>8). After extraction (dichloromethane), washing (water) and drying (magnesium sulphate), the crude product is flash-chromatographed (EtOAc eluent). N-[2-(5-Methoxyindol-3-yl)ethyl]diacetamide (4) (300 mg, 50% yield) is obtained.

Workup

  1. temperatureThe mixture is heated for 72 h
  2. customThe solvent is evaporated off
  3. extractionAfter extraction (dichloromethane)
  4. washwashing (water)
  5. dry with materialdrying (magnesium sulphate)
  6. customthe crude product is flash-chromatographed (EtOAc eluent)

Sources & evidence

ORD record
ord-8a236f1593674321bb6c343b8c23bcb0
Source dataset
uspto-grants-2000_10
Patent number
US06140372

Linked notes

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