1-Fluoro-3-iodobenzene → 1-[3-(3-Fluorophenyl)-2-propynyl]4-methylpiperidine

HRID 6790

Reaktionsgleichung

Reaktionsgleichung von HRID 6790
[F:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[CH:6][CH:7]=1.[CH3:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]#[CH:18])[CH2:12][CH2:11]1>C(NCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu]I.C1(C)C(C(P(C(C2C(C)=CC=CC=2)=O)C(C2C(C)=CC=CC=2)=O)=O)=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:18]#[C:17][CH2:16][N:13]2[CH2:14][CH2:15][CH:10]([CH3:9])[CH2:11][CH2:12]2)[CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 2

HCID 707251-Fluoro-3-iodobenzeneHCID 113555094-Methyl-1-(prop-2-yn-1-yl)piperidine

Produkt 1

HCID 98994381-[3-(3-Fluorophenyl)-2-propynyl]4-methylpiperidineAusbeute 56,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 19696886Tri(o-toluoyl)phosphineKatalysatorHCID 8021DiethylamineLösungsmittel

Versuchsvorschrift

A mixture of 3-fluoroiodobenzene (8.88 g), 4-methyl-1-(2-propynyl)piperidine (6.80 g), palladium acetate (0.045 g), tri-o-toloylphosphine (0.24 g) and copper(I) iodide (0.1 g) in dry diethylamine (50 ml) was heated under reflux for 5 hours. The solvent was removed under reduced pressure and the residue was taken up in diethyl ether and washed with water. The organic phase was dried over magnesium sulfate and the solvent was removed under reduced pressure. Distillation of the residue under reduced pressure gave an oil (5.20 g) of boiling point 105° C./0.07 mm Hg.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. customThe solvent was removed under reduced pressure
  4. washwashed with water
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. distillationDistillation of the residue under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-407eb598551c4c3b88f8f45387ed5837
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084158B2

Verknüpfte Notizen

Wird geladen…