Aniline → N-[1-(Phenylmethyl)-4-piperidinylidene]benzenamine

HRID 1885720Notes

Reaction equation

HRID 1885720 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[N:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6115AnilineHCID 51700761-Benzyl-2-piperidone

Product 1

HCID 13860895N-[1-(Phenylmethyl)-4-piperidinylidene]benzenamineYield 65%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A 1000 ml round bottom flask affixed with a stirring bar, a Dean-Stark trap and a condenser was charged with 101.6 g of benzylpiperidone, 500 ml of toluene, 50 g of aniline and 500 mg of p-toluene sulfonic acid. The mixture was refluxed overnight. After removal of the solvent, the reaction mixture was poured into 600 ml of isopropyl ether. The resulting solution was filtered, and the filtrate concentrated and then vacuum distilled at 185°-190° C., 1.25 torr to obtain 91.9 g (about 65% yield) of product as a light yellow oil.

Workup

  1. customA 1000 ml round bottom flask affixed with a stirring bar
  2. temperatureThe mixture was refluxed overnight
  3. customAfter removal of the solvent
  4. additionthe reaction mixture was poured into 600 ml of isopropyl ether
  5. filtrationThe resulting solution was filtered
  6. concentrationthe filtrate concentrated
  7. distillationvacuum distilled at 185°-190° C.

Sources & evidence

ORD record
ord-8b5809c6ad374b10a5bddd9673c4ab7d
Source dataset
uspto-grants-1992_09
Patent number
US05145967

Reaction notes

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