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

HRID 1885720Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1885720
[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

Komponenten

5

Edukt 2

HCID 6115AnilineHCID 51700761-Benzyl-2-piperidone

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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.

Quellen und Nachweise

ORD-Eintrag
ord-8b5809c6ad374b10a5bddd9673c4ab7d
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05145967

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