Ethyl 5-[4-(1-methylethyl)phenyl]pyridine-3-carboxylate → Ethyl 5-[4-(1-methylethyl)phenyl]piperidine-3-carboxylate

HRID 1642789Notes

Reaction equation

HRID 1642789 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:13]=[N:14][CH:15]=2)=[CH:6][CH:5]=1)[CH3:3].[H][H]>C(O)C.[Pd]>[CH3:3][CH:2]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[CH2:15][NH:14][CH2:13][CH:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11]2)=[CH:8][CH:9]=1)[CH3:1]

Participants

5

Reactant 2

HCID 58002314Ethyl 5-[4-(1-methylethyl)phenyl]pyridine-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 58002566Ethyl 5-[4-(1-methylethyl)phenyl]piperidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2.4 g (8.9 mmol) of ethyl 5-[4-(1-methylethyl)phenyl]pyridine-3-carboxylate were dissolved in 60 ml of ethanol, 1.33 g Pd/C (10%) were added and the mixture was hydrogenated in an autoclave at 60° C. at a hydrogen pressure of 50 bar overnight. The reaction mixture was filtered through silica gel. The resulting solution was concentrated under reduced pressure. Water was added to the residue and the solution was adjusted to pH 8 using aqueous 1 N sodium hydroxide solution. The mixture was then extracted with dichloromethane. The organic phase was dried over sodium sulphate and concentrated. Yield: 2.1 g (81% of theory)

Workup

  1. filtrationThe reaction mixture was filtered through silica gel
  2. concentrationThe resulting solution was concentrated under reduced pressure
  3. additionWater was added to the residue
  4. extractionThe mixture was then extracted with dichloromethane
  5. dry with materialThe organic phase was dried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-40ef2f27dd9a49bf80e849892a4e5173
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

Loading…