Methyl [5-(4-ethylphenyl)pyridin-3-yl]carbamate → Methyl [5-(4-ethylphenyl)piperidin-3-yl]carbamate

HRID 876229Notes

Reaction equation

HRID 876229 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([NH:15][C:16](=[O:19])[O:17][CH3:18])[CH:12]=[N:13][CH:14]=2)=[CH:5][CH:4]=1)[CH3:2]>C(O)C.C(O)(=O)C>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][NH:13][CH2:12][CH:11]([NH:15][C:16](=[O:19])[O:17][CH3:18])[CH2:10]2)=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 68074774Methyl [5-(4-ethylphenyl)pyridin-3-yl]carbamate

Product 1

HCID 68074779Methyl [5-(4-ethylphenyl)piperidin-3-yl]carbamate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 1.0 g (3.7 mmol) of methyl [5-(4-ethylphenyl)pyridin-3-yl]carbamate in 100 ml of ethanol and 100 ml of acetic acid was reacted according to General Method 5A. The solution was concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel, dichloromethane/methanol 4:1). Yield: 171 mg (16% of theory)

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customThe crude product was purified by flash chromatography (silica gel, dichloromethane/methanol 4:1)

Sources & evidence

ORD record
ord-59703bc2af8847beac33b1bdfb8a9cfc
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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