Benzyl Bromide → Ethyl 4-benzylpiperidine-4-carboxylate

HRID 2360588Notes

Reaction equation

HRID 2360588 reaction equation
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O.O>[CH2:18]([C:4]1([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2][NH:1][CH2:11][CH2:10]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 53297794Ethyl 4-benzylpiperidine-4-carboxylateYield 86.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of ethyl isonipecotate (65 mmol; 10.2 g), anhydrous potassium carbonate (195 mmol; 26.9 g) and benzyl bromide (78 mmol; 13.36 g) in anhydrous N,N-dimethylformamide (100 ml) was stirred at 70° C. for 18 hours. After cooling, the reaction mixture was diluted with water (300 ml) and extracted with ethyl acetate (3×200 ml). The combined organic phases were washed with saturated NaCl solution (3×100 ml), dried over sodium sulfate and evaporated under reduced pressure. A crude product was obtained, which was purified on a column of alumina (eluting with chloroform) to give 13.84 g (86%) of pure product as a yellow oil.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (3×200 ml)
  3. washThe combined organic phases were washed with saturated NaCl solution (3×100 ml)
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customA crude product was obtained
  7. customwhich was purified on a column of alumina (eluting with chloroform)

Sources & evidence

ORD record
ord-efbfa8c995b54d329be042e82b422e8f
Source dataset
uspto-grants-2014_04
Patent number
US08686147B2

Reaction notes

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