Triethylamine → 4-(Acetylthio)-1-[(E)-4-(trifluoromethoxy)cinnamoyl]-piperidine

HRID 1601364Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1601364
Cl.[C:2]([S:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)(=[O:4])[CH3:3].C(N(CC)CC)C.[F:19][C:20]([F:34])([F:33])[O:21][C:22]1[CH:32]=[CH:31][C:25](/[CH:26]=[CH:27]/[C:28](Cl)=[O:29])=[CH:24][CH:23]=1>ClCCl>[C:2]([S:5][CH:6]1[CH2:11][CH2:10][N:9]([C:28](=[O:29])/[CH:27]=[CH:26]/[C:25]2[CH:24]=[CH:23][C:22]([O:21][C:20]([F:33])([F:34])[F:19])=[CH:32][CH:31]=2)[CH2:8][CH2:7]1)(=[O:4])[CH3:3]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 5709512(E)-3-[4-(trifluoromethoxy)phenyl]prop-2-enoyl chlorideHCID 183632904-(Acetylthio)piperidine hydrochloride

Produkt 1

HCID 183632734-(Acetylthio)-1-[(E)-4-(trifluoromethoxy)cinnamoyl]-piperidineAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

In 17 ml of dichloromethane were suspended 1.28 g (6.53 mmol) of 4-(acetylthio)piperidine hydrochloride, and 2.27 ml (16.3 mmol) of triethylamine were added dropwise to the suspension with stirring under ice-cooling. Then, a solution in which 1.80 g (7.18 mmol) of (E)-4-(trifluoromethoxy)cinnamoyl chloride were dissolved in 6 ml of dichloromethane was added dropwise to the reaction mixture, followed by stirring of the mixture at the same temperature for 1 hour. The reaction mixture was subjected to silica gel column chromatography and eluted with a mixed solvent of hexane-ethyl acetate (2:1 to 1:1) to obtain 2.32 g (yield: 95%) of the desired compound as a slightly yellow solid.

Aufarbeitung

  1. additionwere added dropwise to the suspension
  2. temperaturecooling
  3. additionwas added dropwise to the reaction mixture
  4. stirringby stirring of the mixture at the same temperature for 1 hour
  5. washeluted with a mixed solvent of hexane-ethyl acetate (2:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-8e4484be044e49e8b8f7c520ec3f4b1c
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05977152

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