Benzyl Bromide → Ethyl 1-benzylpiperidine-4-carboxylate

HRID 966418Notes

Reaction equation

HRID 966418 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:9]1[CH2:19][CH2:18][CH:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][CH2:10]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([N:9]1[CH2:19][CH2:18][CH:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

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

Product 1

HCID 90423Ethyl 1-benzylpiperidine-4-carboxylateYield 74.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

30 g of benzyl bromide are added dropwise to a mixture of 25 g of ethyl isonipecotate and 25 g of K2CO3 in 125 ml of DMF, while maintaining the temperature of the reaction mixture between 25 and 30° C., and the resulting mixture is then stirred at RT for 1 hour. The reaction mixture is poured onto 1 liter of ice-cold water and extracted twice with ether, the organic phase is washed with water and dried over MgSO4, and the solvent is evaporated off under vacuum. The resulting oil obtained is distilled off under reduced pressure. 29.2 g of the expected product are obtained; b.p.=120-122° C. at 2.7 Pa.

Workup

  1. temperaturewhile maintaining the temperature of the reaction mixture between 25 and 30° C.
  2. extractionextracted twice with ether
  3. washthe organic phase is washed with water
  4. dry with materialdried over MgSO4
  5. customthe solvent is evaporated off under vacuum
  6. customThe resulting oil obtained
  7. distillationis distilled off under reduced pressure

Sources & evidence

ORD record
ord-9a71b7f294e24d63b42ba84c7ca1bd3f
Source dataset
uspto-grants-2005_10
Patent number
US06951940B2

Reaction notes

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