Ammonium formate → Tert-butyl 4-(2-cyanophenyl)piperidine-1-carboxylate

HRID 238268

Reaction equation

HRID 238268 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]#[N:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>[Pd].O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]#[N:21])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 18326592tert-butyl 4-(2-cyanophenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 18326585Tert-butyl 4-(2-cyanophenyl)piperidine-1-carboxylateYield 74.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

4-(2-Cyano-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.2 g) was dissolved in IMS (15 mL) and palladium on carbon (10%; 0.08 g) in water (0.5 mL) was added. Ammonium formate (0.3 g) was added and the mixture heated at reflux for 0.5 hour. The mixture was allowed to cool, filtered and the solvent removed by evaporation to give the title compound as a clear colourless oil (0.15 g). LCMS m/z 287.3[M+H]+. R.T.=4.63 min (Analytical Method 4).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 0.5 hour
  3. temperatureto cool
  4. filtrationfiltered
  5. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-6c6b8b24a291417584e13c73563824ae
Source dataset
uspto-grants-2014_02
Patent number
US08642621B2

Linked notes

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