Methyl 4-(4-pyridinyl)benzoate → Methyl 4-(piperidin-4-yl)benzoate

HRID 1675094Notes

Reaction equation

HRID 1675094 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1>CO.[Pd]>[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 5152686Methyl 4-(4-pyridinyl)benzoate

Product 1

HCID 24904226Methyl 4-(piperidin-4-yl)benzoateYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl 4-(pyridin-4-yl)benzoate (285 g, 1336.57 mmol) and palladium (5% on carbon, 50% wet, JM Type 87L) (57 g, 13.39 mmol) in methanol (2850 mL) were stirred under an atmosphere of hydrogen at 5 bar and 70° C. for 15 hours. The catalyst was removed by filtration and washed with methanol (2850 mL). The solvent was evaporated to dryness to afford methyl 4-(piperidin-4-yl)benzoate (291 g, 99%) as a solid.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with methanol (2850 mL)
  3. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-3a70a2d339144f47b8c0ec995a17ae40
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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