HCID 18473954, compound → 2-(Dimethylamino)-5-[1-(4-hydroxy-1H-indol-3-yl)ethyl]-4(5H)-oxazolone

HRID 2227525Notes

Reaction equation

HRID 2227525 reaction equation
C([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11]([CH:18]([CH:20]1[O:24][C:23]([N:25]([CH3:27])[CH3:26])=[N:22][C:21]1=[O:28])[CH3:19])=[CH:12][NH:13]2)C1C=CC=CC=1>C(O)C.O1CCCC1.[C].[Pd]>[CH3:27][N:25]([CH3:26])[C:23]1[O:24][CH:20]([CH:18]([C:11]2[C:10]3[C:14](=[CH:15][CH:16]=[CH:17][C:9]=3[OH:8])[NH:13][CH:12]=2)[CH3:19])[C:21](=[O:28])[N:22]=1

Participants

5

Reactant 1

HCID 18473954HCID 18473954, compound

Product 1

HCID 184739322-(Dimethylamino)-5-[1-(4-hydroxy-1H-indol-3-yl)ethyl]-4(5H)-oxazoloneYield 61.3%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-[1-(4-benzyloxyindol-3-yl)ethyl]-2-dimethylamino-2-oxazolin-4-one (268 mg) was dissolved in a mixture of ethanol and tetrahydrofuran (7:3.10 ml). 10% palladium-carbon (80 mg) was added and the whole was hydrogenated for 5 hours at room temperature under normal pressure. The catalyst was removed from the mixture and 10% palladium-carbon (80 mg) was added again. The whole was hydrogenated for additional 24 hours at room temperature under normal pressure. The reaction mixture was filtered to remove the catalyst. The filtrate was concentrated to give 2-dimethylamino-5-[1-(4-hydroxyindol-3-yl)ethyl]-2-oxazolin-4-one (125 mg).

Workup

  1. customThe catalyst was removed from the mixture and 10% palladium-carbon (80 mg)
  2. additionwas added again
  3. waitThe whole was hydrogenated for additional 24 hours at room temperature under normal pressure
  4. filtrationThe reaction mixture was filtered
  5. customto remove the catalyst
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7695602f633c4f3ebd5f9baddeae1fd7
Source dataset
uspto-grants-2002_07
Patent number
US06414003B1

Reaction notes

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