Potassium Carbonate → 3-(4-Bromophenyl)piperidine

HRID 251799Notes

Reaction equation

HRID 251799 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]1([CH:15]2[CH2:20][CH2:19][CH2:18][NH:17][CH2:16]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>S(=O)(=O)(O)O>[Br:1][C:12]1[CH:13]=[CH:14][C:9]([CH:15]2[CH2:20][CH2:19][CH2:18][NH:17][CH2:16]2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 1072073-Phenylpiperidine

Product 1

HCID 468353263-(4-Bromophenyl)piperidineYield 28.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
70 °C

Procedure

N-Bromosuccinimide (912 mg, 5.12 mmol) was added to a solution of 1.18 g (7.32 mmol) of 3-phenylpiperidine in 50% sulfuric acid (12 ml), and the mixture was stirred at 70° C. for 30 min. A saturated aqueous potassium carbonate solution was added to the reaction solution under ice cooling, and the mixture was extracted twice with diethyl ether. The organic layer was dried over anhydrous sodium sulfate, was filtered, and was then concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (chloroform:methanol:concentrated aqueous ammonia=9:0.6:0.06) to give 352 mg (yield 20%) of the title compound.

Workup

  1. extractionthe mixture was extracted twice with diethyl ether
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationwas filtered
  4. concentrationwas then concentrated under the reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (chloroform:methanol:concentrated aqueous ammonia=9:0.6:0.06)

Sources & evidence

ORD record
ord-598b245cac244a30a6d877f4be27d786
Source dataset
uspto-grants-2011_01
Patent number
US07867980B2

Reaction notes

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