1-(4-Nitrobenzyl)piperidine → 4-(Piperidin-1-ylmethyl)aniline

HRID 552125

Reaction equation

HRID 552125 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>C1COCC1.[Ni]>[N:9]1([CH2:8][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:16][CH:15]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 7835411-(4-Nitrobenzyl)piperidineHCID 178418361HCID 178418361, compound

Product 1

HCID 8461504-(Piperidin-1-ylmethyl)aniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.22 g (1.0 mmol, 1.0 eq.) of 1-(4-nitrobenzyl)piperidine (I-27) in 20 mL of THF was added ˜30 mg of Raney Nickel. The reaction mixture was stirred under at room temperature under 1 atm. of hydrogen for 12 h. The reaction mixture was through Celite® and the solvent removed in vacuo to provide 4-(piperidin-1-ylmethyl)benzenamine (I-28).

Workup

  1. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-92dcc1ce91b347c7bc84e34fbff6c632
Source dataset
uspto-grants-2011_05
Patent number
US07951803B2

Linked notes

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