4-(4-Piperidyl)pyridine → HCID 59909821, compound

HRID 1279832Notes

Reaction equation

HRID 1279832 reaction equation
[C:1]([O:5][C:6](=[O:28])[CH2:7][C@H:8]([C:18]1[O:22][N:21]=[C:20]([C:23](OCC)=[O:24])[N:19]=1)[CH2:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)([CH3:4])([CH3:3])[CH3:2].[N:29]1[CH:34]=[CH:33][C:32]([CH:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)=[CH:31][CH:30]=1>C(O)C>[CH:12]1([CH2:11][CH2:10][CH2:9][C@@H:8]([C:18]2[O:22][N:21]=[C:20]([C:23]([N:38]3[CH2:39][CH2:40][CH:35]([C:32]4[CH:31]=[CH:30][N:29]=[CH:34][CH:33]=4)[CH2:36][CH2:37]3)=[O:24])[N:19]=2)[CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:28])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 11395974-(4-Piperidyl)pyridine2×HCID 59909797ethyl 5-{(1R)-1-[2-(tert-butoxy)-2-oxoethyl]4-cyclohexylbutyl}-1,2,4-oxadiazole-3-carboxylate

Product 1

HCID 59909821HCID 59909821, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 5-{(1R)-1 -[2-(tert-butoxy)-2-oxoethyl]4-cyclohexylbutyl}-1,2,4-oxadiazole-3-carboxylate (Preparation 3) (0.50 g, 1.27 mmol) in ethanol (10 ml) was treated with 4-(4-pyridinyl)piperidine (Monatsh.Chem.; 3; 1882; 867) (0.41 g, 2.54 mmol) and the resulting mixture was heated under reflux under a nitrogen atmosphere for 72 hours. Further 4-(4-pyridinyl)piperidine (0.21 g, 1.27 mmol) was added and the mixture heated under reflux for 24 hours. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and water. The layers were separated and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed sequentially with water and brine, dried over anhydrous sodium sulphate, filtered and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (99:1) gradually changing to dichloromethane:methanol (95:5) to afford the title compound as a pale yellow oil (0.39 g).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux under a nitrogen atmosphere for 72 hours
  3. temperaturethe mixture heated
  4. temperatureunder reflux for 24 hours
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was partitioned between ethyl acetate and water
  7. customThe layers were separated
  8. extractionthe aqueous layer extracted with ethyl acetate
  9. washThe combined organic layers were washed sequentially with water and brine
  10. dry with materialdried over anhydrous sodium sulphate
  11. filtrationfiltered
  12. customthe solvent removed under reduced pressure
  13. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (99:1)

Sources & evidence

ORD record
ord-38304f5ae52d4a3f8293cc593ca9564f
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

Loading…