2-Bromopropiophenone → 5Benzyloxy-3-methyl-2-phenyl-1H-indole

HRID 66822

Reaction equation

HRID 66822 reaction equation
Br[CH:2]([CH3:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[CH2:12]([O:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(N(CC)CC)C>[CH2:12]([O:19][C:20]1[CH:21]=[C:22]2[C:23](=[CH:25][CH:26]=1)[NH:24][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[C:2]2[CH3:11])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 164522-BromopropiophenoneHCID 228604-Benzyloxyaniline

Product 1

HCID 218823405Benzyloxy-3-methyl-2-phenyl-1H-indole

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

An amount of 3.6 g (0.015 mole) of 2-bromo-propiophenone and 6 g (0.03 mole) of 4-benzyloxy-aniline were refluxed for two hours in 15 ml of triethylamine. The mixture was evaporated to dryness, and the residue was heated for two hours to 180° C. After cooling, the residue was mixed with 10% hydrochloric acid and extracted with chloroform. The extracts were dried over sodium sulfate, filtered, and evaporated. The residue obtained was purified by column chromatography on silicagel with toluene as solvent.

Workup

  1. customThe mixture was evaporated to dryness
  2. temperaturethe residue was heated for two hours to 180° C
  3. temperatureAfter cooling
  4. additionthe residue was mixed with 10% hydrochloric acid
  5. extractionextracted with chloroform
  6. dry with materialThe extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue obtained
  10. customwas purified by column chromatography on silicagel with toluene as solvent

Sources & evidence

ORD record
ord-99133378138d4a53a7c17c71f1a63b52
Source dataset
uspto-grants-1982_08
Patent number
US04343811

Linked notes

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