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Melatonin → HCID 15382325, compound

HRID 370055
Notes
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Reaction equation

HRID 370055 reaction equation
[CH3:1][C:2]([NH:4][CH2:5][CH2:6][C:7]1[C:11]2[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:10]=2[NH:9][CH:8]=1)=[O:3].[H-].[Na+].[C:20](Cl)(=[O:22])[CH3:21].[O:24]1CC[CH2:26][CH2:25]1>>[C:20]([N:9]1[C:10]2[C:11](=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[C:7]([CH2:6][CH2:5][NH:4][C:2](=[O:3])[CH3:1])=[CH:8]1)(=[O:22])[CH3:21].[C:20]([N:9]1[C:10]2[C:11](=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[C:7]([CH2:6][CH2:5][N:4]([C:25]([CH3:26])=[O:24])[C:2](=[O:3])[CH3:1])=[CH:8]1)(=[O:22])[CH3:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 896MelatoninHCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 24758Sodium hydride

Product 2

HCID 15382325HCID 15382325, compoundHCID 44359266N-[2-(1-acetyl-5-methoxyindol-3-yl)ethyl]diacetamide

Procedure

Melatonin (126 mg) is dissolved in tetrahydrofuran (10 ml) in a 50 ml round-bottomed flask, sodium hydride (200 mg) is then added and the mixture is maintained at reflux (10 min). After cooling (0° C.), acetyl chloride is added and the mixture is kept stirring overnight (room temperature). After filtration and dilution (EtOAc), the organic phase is washed with water and then separated on a silica plate. N-[2-(1-Acetyl-5-methoxyindol-3-yl)ethyl]acetamide (1) is mainly obtained, along with a side product, N-[2-(1-acetyl-5-methoxyindol-3-yl)ethyl]diacetamide (10) (cf. Example 10).

Workup

  1. temperaturethe mixture is maintained
  2. temperatureat reflux (10 min)
  3. additionis added
  4. filtrationAfter filtration and dilution (EtOAc)
  5. washthe organic phase is washed with water
  6. customseparated on a silica plate

Sources & evidence

ORD record
ord-707afcc28a634645995c8dc135c38eae
Source dataset
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06140372

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes