Toluene → N-[1-(phenylmethyl)-4-piperidinylidene]-3-pyridinamine

HRID 28124Notes

Reaction equation

HRID 28124 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=1.CC1C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>O>[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][C:11](=[N:21][C:17]3[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 100093-AminopyridineHCID 192201-Benzyl-4-piperidone

Product 1

HCID 10706822N-[1-(phenylmethyl)-4-piperidinylidene]-3-pyridinamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 19 parts of 1-(phenylmethyl)-4-piperidinone, 11.8 parts of 3-pyridinamine, 120 parts of methylbenzene and a small volume of 4-methylbenzenesulfonic acid is stirred and refluxed for 5 hours. (The reaction vessel is provided with reflux-condensor and water-separator). After the calculated amount of water is separated, the solvent is evaporated. The oily residue is dissolved in 800 parts of 2,2'-oxybispropane and evaporated again, yielding 27 parts of N-[1-(phenylmethyl)-4-piperidinylidene]-3-pyridinamine as a yellow-brown oil.

Workup

  1. temperaturerefluxed for 5 hours
  2. custom(The reaction vessel is provided
  3. temperaturewith reflux-condensor
  4. customAfter the calculated amount of water is separated
  5. customthe solvent is evaporated
  6. dissolutionThe oily residue is dissolved in 800 parts of 2,2'-oxybispropane
  7. customevaporated again

Sources & evidence

ORD record
ord-699b85be31244c90849a82aab9a3aa96
Source dataset
uspto-grants-1980_09
Patent number
US04225606

Reaction notes

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