3-Phenylprop-2-enoyl chloride → 2'-[2-(1-Methyl-2-piperidyl)ethyl]-cinnamanilide

HRID 1579348Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1579348
[C:1](Cl)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:12][C:13]1[CH:27]=[CH:26][CH:25]=[CH:24][C:14]=1[CH2:15][CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][N:18]1[CH3:23]>N1C=CC=CC=1>[CH3:23][N:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH:17]1[CH2:16][CH2:15][C:14]1[CH:24]=[CH:25][CH:26]=[CH:27][C:13]=1[NH:12][C:1](=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

4

Edukt 2

HCID 660233-Phenylprop-2-enoyl chlorideHCID 110852822-(2-Aminophenethyl)-1-methylpiperidine

Produkt 1

HCID 209816792'-[2-(1-Methyl-2-piperidyl)ethyl]-cinnamanilideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Cinnamoyl chloride (6.0 g., 0.036 mole) is added to a solution of 2-(o-aminophenethyl)-1-methylpiperidine (7.8 g., 0.036 mole) in 100 ml. of pyridine in one portion with vigorous stirring. Stirring is continued for 3 hours and the pyridine solution is then concentrated in vacuo. The resulting residue is taken up in 150 ml. of water and made basic with 40% sodium hydroxide. The basified solution is extracted with several 200 ml. portions of ether, which are combined, washed with water, dried over magnesium sulfate and the ether solvent evaporated. The residue thus obtained crystallizes and is further purified by crystallizing from isopropyl ether providing 8.7 g. (70% yield) of analytically pure 2'-[2-(1-methyl-2-piperidyl)ethyl]cinnamanilide melting at 101.5°-103.5°C. (corr.).

Aufarbeitung

  1. concentrationthe pyridine solution is then concentrated in vacuo
  2. extractionThe basified solution is extracted with several 200 ml
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe ether solvent evaporated
  6. customThe residue thus obtained
  7. customcrystallizes
  8. customis further purified
  9. customby crystallizing from isopropyl ether providing 8.7 g

Quellen und Nachweise

ORD-Eintrag
ord-58e31808325643b8869abcd34e4e2cd9
Quelldatensatz
uspto-grants-1976_01
Patentnummer
US03931195

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