2-Iodotoluene → 1-(3-o-Tolyl-2-propynyl)piperidine

HRID 6788

Reaktionsgleichung

Reaktionsgleichung von HRID 6788
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].[CH2:9]([N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[C:10]#[CH:11]>C(NCC)C.Cl[Pd-2](Cl)(P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:3]1([CH3:8])[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:11]#[C:10][CH2:9][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Komponenten

6

Edukt 2

HCID 51282-IodotolueneHCID 3366521-(Prop-2-yn-1-yl)piperidine

Produkt 1

HCID 120567831-(3-o-Tolyl-2-propynyl)piperidineAusbeute 62,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418903HCID 178418903, VerbindungKatalysatorHCID 8021DiethylamineLösungsmittel

Versuchsvorschrift

A mixture of 2-iodotoluene (6.54 g), N-(2-propynyl)piperidine (3.69 g), dichlorobis(triphenylphosphino)palladium(II) (0.05 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 concentrated completely under reduced pressure. Distillation of the residue under reduced pressure gave 3.98 g of an oil of boiling point 96–98° C./0.08 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. concentrationconcentrated completely under reduced pressure
  7. distillationDistillation of the residue under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0f8d0671097c4c1fb7b5e5e1778ceb8b
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084158B2

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