1-Methyl-4-piperidone → N'-(1-Methyl-piperidin-4-ylidene)-N-[2-(6-methyl-pyridin-3-yl)-ethyl]-N-p-tolyl-hydrazine

HRID 2369262Notes

Reaction equation

HRID 2369262 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[NH2:11])=[CH:4][CH:3]=1.[CH3:19][N:20]1[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]1>C1C=CC=CC=1>[CH3:19][N:20]1[CH2:25][CH2:24][C:23](=[N:11][N:10]([CH2:9][CH2:8][C:5]2[CH:6]=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[C:12]2[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=2)[CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 740491-Methyl-4-piperidoneHCID 28275201-(4-Methylphenyl)-1-[2-(6-methylpyridin-3-yl)ethyl]hydrazine

Product 1

HCID 49765790N'-(1-Methyl-piperidin-4-ylidene)-N-[2-(6-methyl-pyridin-3-yl)-ethyl]-N-p-tolyl-hydrazine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The crude N-[2-(6-methyl-pyridin-3-yl)-ethyl]-N-p-tolyl-hydrazine was dissolved in benzene (20 cm3) and 4 Å molecular sieves added (˜5 g), followed by 1-methylpiperidin-4-one (346 μL, 3.0 mmol). The reaction was heated to reflux for 2 hours, cooled, and filtered. Solvent was removed in vacuo to yield a crude orange oil.

Workup

  1. addition4 Å molecular sieves added (˜5 g)
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 2 hours
  4. temperaturecooled
  5. filtrationfiltered
  6. customSolvent was removed in vacuo
  7. customto yield a crude orange oil

Sources & evidence

ORD record
ord-112ea48064524b4e8fcdf1b792b423ab
Source dataset
uspto-grants-2014_04
Patent number
US08703952B2

Reaction notes

Loading…