Piperidine → 2-Bromo-4-(piperidin-1-yl)benzaldehyde

HRID 1040407Notes

Reaction equation

HRID 1040407 reaction equation
[Br:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[Br:1][C:2]1[CH:9]=[C:8]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

7

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 27733192-Bromo-4-fluorobenzaldehyde

Product 1

HCID 71486452-Bromo-4-(piperidin-1-yl)benzaldehydeYield 90%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-bromo-4-fluorobenzaldehyde (300 mg, 1.48 mmol) in 3.0 mL of N,N-dimethylformamide was added potassium carbonate (204 mg, 1.48 mmol), piperidine (154 μL, 1.55 mmol) at room temperature. After being stirred at 110° C. overnight, the reaction mixture was diluted with a 2:1 solution of ethyl acetate and hexane. The solution was washed with water, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 to 75/25) to obtain the title compound (355 mg, 90%).

Workup

  1. washThe solution was washed with water, brine
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 to 75/25)

Sources & evidence

ORD record
ord-7483ec2820cf4b6d933f08232424ce75
Source dataset
uspto-grants-2013_10
Patent number
US08552220B2

Reaction notes

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