Ethyl bromoacetate → 1-Piperidineacetic acid, ethyl ester

HRID 2060649Notes

Reaction equation

HRID 2060649 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[N:8]1([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8082PiperidineHCID 8471Triethylamine

Product 1

HCID 6434661-Piperidineacetic acid, ethyl esterYield 64%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Ethyl bromoacetate (8.5 g, 50.9 mmol) was added dropwise to a stirred solution of piperidine (4.3 g, 50.5 mmol) and triethylamine (5.5 g, 54.4 mmol) in chloroform (20 ml) at such a rate as to maintain a gentle reflux. After the addition was complete stirring was continued for 2 hours and the reaction mixture washed with water (20 ml×3). The chloroform layer was dried (MgSO4) filtered and the solvent evaporated to leave a yellow oil. This oil was passed through a short column of silica eluting with a CH2Cl2/Pet Ether 40:60 mixture (1:1). Removal of the solvent from the resulting solution gave the required product as a pale yellow oil (Yield 5.5 g, 64%).

Workup

  1. temperatureto maintain a gentle reflux
  2. additionAfter the addition
  3. washthe reaction mixture washed with water (20 ml×3)
  4. dry with materialThe chloroform layer was dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customto leave a yellow oil
  8. customRemoval of the solvent from the resulting solution

Sources & evidence

ORD record
ord-3d7677161dca40dfb403abac87844148
Source dataset
uspto-grants-2012_10
Patent number
US08278448B2

Reaction notes

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