Acetic Acid → 4-Anilinopiperidine

HRID 1948982Notes

Reaction equation

HRID 1948982 reaction equation
O.Cl.[NH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(O)(=O)C>[Zn].O>[NH:10]([CH:6]1[CH2:7][CH2:8][NH:3][CH2:4][CH2:5]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 6115AnilineHCID 2723901Piperonylamine

Product 1

HCID 899824-Anilinopiperidine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

In a three neck round bottom flask equipped with mechanical stirrer and water condenser, 15.36 gm (0.10 moles) of 4-piperidone hydrochloride monohydrate and 16.43 gm (0.2 moles) of aniline were added. To this mixture, 130 gm (2.0 moles) of zinc and 120 gm (2.00 moles) of 90% acetic acid were added. The reaction mixture was stirred at room temperature for 24 hrs and at 50 to 70° C. for 24 hrs. Water was then added to the reaction mixture and filtered. Crushed ice was added to the filtrate and was neutralized with excess of aqueous sodium hydroxide solution. The crude 4-anilinopiperidine was obtained by filtration.

Workup

  1. customIn a three neck round bottom flask equipped with mechanical stirrer and water condenser
  2. filtrationfiltered
  3. additionCrushed ice was added to the filtrate

Sources & evidence

ORD record
ord-27b27680bf544a84bb01b60db0a67b8a
Source dataset
uspto-grants-2013_03
Patent number
US08399677B2

Reaction notes

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