Allylamine → N-2-Propen-1-yl-6-[4-(trifluoromethyl)phenyl]-2-pyridinamine

HRID 1269670Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1269670
[CH2:1]([NH2:4])[CH:2]=[CH2:3].Br[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[N:7]=1>C(O)C.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:1]([NH:4][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:21])[F:20])=[CH:14][CH:13]=2)[N:7]=1)[CH:2]=[CH2:3]

Komponenten

5

Edukt 2

HCID 7853AllylamineHCID 184483252-Bromo-6-(4-(trifluoromethyl)phenyl)pyridine

Produkt 1

HCID 18448421N-2-Propen-1-yl-6-[4-(trifluoromethyl)phenyl]-2-pyridinamineAusbeute 74,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24462Copper SulfateKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of of allylamine (0.447 mL, 5.96 mmol) and 2-bromo-6-[4-(trifluoromethyl)phenyl]pyridine (0.1 g, 0.298 mmol) in ethanol (5 mL) were heated at 100° C. in a 25 mL pressure vessel. After heating overnight the reaction was cooled and copper sulfate was added and heating continued at 100° C. overnight. After this time the reaction was allowed to coole to room temperature and concentrated in vacuo. Purification by SPE (Silica, 10 g) eluting 3:1 cyclohexane:chloroform afforded the title compound as a dark yellow solid (0.062 g).

Aufarbeitung

  1. temperatureAfter heating overnight the reaction
  2. temperaturewas cooled
  3. temperatureheating
  4. customto coole to room temperature
  5. concentrationconcentrated in vacuo
  6. customPurification by SPE (Silica, 10 g)
  7. washeluting 3:1 cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-546d2e7ec73a4f6e9519db19b5087601
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199239B2

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