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

HRID 1007120Notes

Reaction equation

HRID 1007120 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>[Zn].C(O)(=O)C>[NH2:1][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

Participants

4

Reactant 1

HCID 7835411-(4-Nitrobenzyl)piperidine

Product 1

HCID 8461504-(Piperidin-1-ylmethyl)aniline

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

An acetic acid (3 ml) solution of the 4-nitrobenzylpiperidine compound (25) (65.8 mg, 0.2 mmol) obtained in the process 2 was added with zinc (300 mg) little by little at 0° C. After having been stirred at the room temperature for 2 hours, this was filtered to be taken out, had the solvent distilled out and neutralized with 2M aqueous sodium hydroxide, and then was extracted with ethylacetate. The resultant was washed with water and the saturated saline solution, dried and then vacuum concentrated, thus obtained a 4-aminobenzylpiperidine compound (26:R=2,2-dimethylcyclopropane) in the form of a yellow oily matter (50 mg, 85%).

Workup

  1. filtrationthis was filtered
  2. distillationdistilled out
  3. extractionwas extracted with ethylacetate
  4. washThe resultant was washed with water
  5. customthe saturated saline solution, dried
  6. concentrationvacuum concentrated

Sources & evidence

ORD record
ord-774164c333074fe0b96959aca8669aa9
Source dataset
uspto-grants-2004_09
Patent number
US06794378B2

Reaction notes

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