Ethanol → 3-(1-Piperidinylmethyl)aniline

HRID 2095098Notes

Reaction equation

HRID 2095098 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[CH2:7][N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)([O-])=O.C(O)C.O.NN>C1COCC1.[Ni]>[N:8]1([CH2:7][C:6]2[CH:5]=[C:4]([NH2:1])[CH:16]=[CH:15][CH:14]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 12254862HCID 12254862, compound

Product 1

HCID 64843313-(1-Piperidinylmethyl)anilineYield 95%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(3-nitrobenzyl)piperidine (263 mg; 1.19 mmol) in THF:ethanol mixture (1:1) (15 mL) was added a catalytical amount of Raney-Nickel and hydrazine hydrate (6.0 mmol) and the mixture was stirred for 15 minutes at ambient temperature, filtered through a Celite-pad and the filtrate was evaporated to provide the title compound (180 mg, 95%), which was used in futher reactions without purification.

Workup

  1. filtrationfiltered through a Celite-pad
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-ec1443ca5002435380ccff3a36561dbd
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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