Water → HCID 20185260, compound

HRID 2309407Notes

Reaction equation

HRID 2309407 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([OH:20])=[C:15]([CH3:21])[CH:14]=1)=[C:7]2[CH3:22].Br.[CH2:24]([N:26]([CH2:30][CH3:31])[CH2:27][CH2:28]Br)[CH3:25].O>CN(C)C=O>[CH2:24]([N:26]([CH2:30][CH3:31])[CH2:27][CH2:28][O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([OH:20])=[C:15]([CH3:21])[CH:14]=1)=[C:7]2[CH3:22])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 706072-Bromoethyldiethylammonium bromideHCID 13938646HCID 13938646, compound

Product 1

HCID 20185260HCID 20185260, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.6 g of 60% sodium hydride was suspended in 50 ml of dimethylformamide, and under ice cooling, 5-hydroxy-2-(4-hydroxy-3,5-dimethylphenyl)-3-methylindole was added. After stirring for 30 minutes, 2.8 g of 2-diethylaminoethylbromide hydrobromide was added. The mixture was stirred for 2 hours. The reaction mixture was poured into cold water, and extracted with ethyl acetate. The extract was purified by silica gel column chromatography, and then subjected to thin-layer chromatography to give 5-(2-diethylaminoethoxy)-2-(4-hydroxy-3,5-dimethylphenyl)-3-methylindole.

Workup

  1. stirringThe mixture was stirred for 2 hours
  2. extractionextracted with ethyl acetate
  3. customThe extract was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7fee1d7e83fe406f957fc5b6bd8946b0
Source dataset
uspto-grants-1987_09
Patent number
US04695581

Reaction notes

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