Potassium Carbonate → HCID 19426622, compound

HRID 741573Notes

Reaction equation

HRID 741573 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].Br[CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:11]([O:10][C:8](=[O:9])[CH2:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][N:1]1[CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 76300Ethyl 4-bromobutyrate2×HCID 4369812-Piperidineacetic acid, ethyl ester

Product 1

HCID 19426622HCID 19426622, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred solution of ethyl piperidin-2-ylacetate (8.0 g, 0.047 mole) and ethyl 4-bromobutyrate (6.7 ml, 0.047 mole) in acetone (100 ml) was treated with potassium carbonate (13 g, 0.094 mole) and heated under reflux for 32 h. A further 1.5 ml of ethyl 4-bromobutyrate and 3 g of potassium carbonate was added and reflux continued for 16 h. The mixture was concentrated in vacuo and the residue treated with water (100 ml) and extracted with ethyl acetate (2×100 ml). The combined extracts were dried (Na2SO4), concentrated in vacuo and the residue chromatographed on silica gel eluting with ether/petrol (60-80) to afford the title compound as a pale yellow oil (11.5 g, 86%)

Workup

  1. temperatureheated
  2. temperatureunder reflux for 32 h
  3. temperaturereflux
  4. concentrationThe mixture was concentrated in vacuo
  5. additionthe residue treated with water (100 ml)
  6. extractionextracted with ethyl acetate (2×100 ml)
  7. dry with materialThe combined extracts were dried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customthe residue chromatographed on silica gel eluting with ether/petrol (60-80)

Sources & evidence

ORD record
ord-2f1e835dfe944755b44af64cd877a8bd
Source dataset
uspto-grants-1996_09
Patent number
US05552398

Reaction notes

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