tert-Butyl 4-(4-chlorophenyl)-4-cyanopiperidine-1-carboxylate → HCID 24828980, compound

HRID 1036323Notes

Reaction equation

HRID 1036323 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)([C:14]#[N:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Ni]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([CH2:14][NH2:15])([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 49760270tert-Butyl 4-(4-chlorophenyl)-4-cyanopiperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 24828980HCID 24828980, compoundYield 71.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-(4-chlorophenyl)-4-cyanopiperidin-1-carboxylic acid tert-butyl ester (0.355 g, 1.107 mmol) in ethanol (20 ml) at room temperature was added Raney Nickel (Raney Nickel 2800, 1 ml) and the suspension stirred under 1 atmosphere of hydrogen for 20 hours. The suspension was filtered through celite and the filtrate concentrated to give the amine as an oil (0.258 g, 69%). LC/MS: (LCT) Rt 5.02 [M—But—NH2]+ 324.

Workup

  1. filtrationThe suspension was filtered through celite
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-54481a443bc14af49d3a9c7c77e8fda7
Source dataset
uspto-grants-2013_10
Patent number
US08546407B2

Reaction notes

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