Reaktion #316594

Reaktionsgleichung

toluene

1-fluoro-4-iodo-benzene

1-ethynyl-cyclohexylamine

diisopropylamine

→

1-[2-(4-fluoro-phenyl)-ethyl]-cyclohexylamine

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONThen the base is distilled off
2. 2
   FiltrationThe insoluble constituents are filtered off
3. 3
   Sonstigethe filtrate is evaporated down
4. 4
   SonstigeThe alkyne thus prepared
5. 5
   SonstigeThe catalyst is separated off
6. 6
   workup.DISSOLUTIONThe crude product is dissolved in ethyl acetate
7. 7
   FiltrationThe precipitated solid is filtered off
8. 8
   Waschenwashed with ethyl acetate

Vorschrift

2.5 g (11.3 mmol) 1-fluoro-4-iodo-benzene, 1.5 g (11.9 mmol) 1-ethynyl-cyclohexylamine, 793 mg (1.13 mmol) PdCl2(PPh3)2, 67 mg (0.35 mmol) copper iodide and 50 mL diisopropylamine are stirred for 2 hours at 70° C. Then the base is distilled off and the residue is combined with ethyl acetate. The insoluble constituents are filtered off and the filtrate is evaporated down. The alkyne thus prepared is dissolved in 35 mL THF and 35 mL toluene and hydrogenated with platinum oxide as catalyst at normal pressure. The catalyst is separated off and the filtrate is freed from the solvent. The crude product is dissolved in ethyl acetate and combined with 10% hydrochloric acid in ethyl acetate. The precipitated solid is filtered off and washed with ethyl acetate. Yield: 1.3 g (45%; hydrochloride); mass spectroscopy: [M+H]+=222.

Quelle