Bromobenzene → HCID 9996016, compound

HRID 1252052Notes

Reaction equation

HRID 1252052 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].Br[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(Cl)(Cl)Cl.[Cu]=O>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:11]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 7961BromobenzeneHCID 11430Potassium CarbonateHCID 27283591-[4-(1H-indol-3-yl)piperidino]ethan-1-one

Product 1

HCID 9996016HCID 9996016, compoundYield 77.5%

Reagents, catalysts & solvents 3

HCID 14829Copper oxideCatalystHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(1-acetyl-4-piperidyl)indole (10.0 g), bromobenzene (6.48 g), potassium carbonate (5.70 g) and copper(II) oxide (0.26 g) in anhydrous N,N-dimethylformamide (10 ml) was refluxed for 30 minutes. The reaction mixture was cooled and diluted with chloroform, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure and the residue was subjected to column chromatography on alumina (400 g) followed by elution with a mixture of toluene and ethyl acetate (20:1 V/V). The fractions containing the desired compound were combined and concentrated under reduced pressure to give 3-(1-acetyl-4-piperidyl)-1-phenylindole (10.19 g).

Workup

  1. temperaturewas refluxed for 30 minutes
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe insoluble material was filtered off
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. washfollowed by elution with a mixture of toluene and ethyl acetate (20:1 V/V)
  6. additionThe fractions containing the desired compound
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4a91f50281c5418d9e6814f93775e029
Source dataset
uspto-grants-1988_05
Patent number
US04742057

Reaction notes

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