Acetic Acid → 4-Anilinopiperidine

HRID 1948976Notes

Reaction equation

HRID 1948976 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

Procedure

To a mixture of 0.5 to 5.0 parts (w/w) of 4-piperidone hydrochloride monohydrate, preferably 1.00 to 3.00 parts (w/w) and 0.5 to 5.0 parts (w/w) of aniline, preferably 1.0 to 2.0 parts (w/w), 1 to 20 parts (w/w) of zinc preferably 4 to 12 parts (w/w) and 5 to 100 parts (w/w) of 90% acetic acid preferably 20 to 50 parts (w/w) were added and stirred at room temperature for 15 to 35 hrs, preferably 20 to 30 hrs, and then at 50 to 90° C., preferably at 65 to 80° C. for 15 to 35 hrs, preferably 20 to 30 hrs. After completion of the reaction, water was 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. It was then recrystallized with acetone to give colorless needles of 4-anilinopiperidine, mp 105-06° C.

Workup

  1. additionwere added
  2. waitat 50 to 90° C., preferably at 65 to 80° C. for 15 to 35 hrs
  3. custompreferably 20 to 30 hrs
  4. additionwas added to the reaction mixture
  5. filtrationfiltered
  6. additionCrushed ice was added to the filtrate
  7. customThe crude 4-anilinopiperidine was obtained by filtration
  8. customIt was then recrystallized with acetone

Sources & evidence

ORD record
ord-270d379aece64edb9d14d85f5117ceb4
Source dataset
uspto-grants-2013_03
Patent number
US08399677B2

Reaction notes

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