(3-Bromopropyl)benzene → HCID 18351837, compound

HRID 430777Notes

Reaction equation

HRID 430777 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7]1.[C:23]1([CH2:29][CH2:30][CH2:31]Br)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[NH4+].[Cl-]>CN(C=O)C>[C:23]1([CH2:29][CH2:30][CH2:31][O:3][CH2:4][CH2:5][N:6]2[C:14]3[C:9](=[C:10]([O:15][CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 12503(3-Bromopropyl)benzeneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 18351819HCID 18351819, compound

Product 1

HCID 18351837HCID 18351837, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon atmosphere, sodium hydride (40 mg) was added to 1-(2-hydroxyethyl)-4-benzyloxyindole (52 mg) in DMF (3 ml) and the mixture was stirred at room temperature for 15 minutes. To the mixture, 3-phenyl-1-bromopropane (0.15 ml) was added and the resultant was stirred at room temperature for another 18 hours. The reaction mixture was added to saturated aqueous NH4Cl solution (5 ml) to stop the reaction, and the resultant was extracted with ethyl acetate (3×10 ml). The obtained organic layers were washed with saturated brine and dried over sodium sulfate. After removing solids by filtration, the solvent was removed under reduced pressure, and the obtained crude product was purified by silica gel column chromatography to obtain the desired compound (72 mg, yield: 96%).

Workup

  1. stirringthe resultant was stirred at room temperature for another 18 hours
  2. customthe reaction
  3. extractionthe resultant was extracted with ethyl acetate (3×10 ml)
  4. washThe obtained organic layers were washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. customAfter removing solids
  7. filtrationby filtration
  8. customthe solvent was removed under reduced pressure
  9. customthe obtained crude product
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b3229e56cac24aabac1809125493d01e
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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