Reaktion #1747825

Reaktionsgleichung

3-Vinyl-cyclohex-2-enone

dipropylamine

KBr

Cs2CO3

→

3-(2-Dipropylamino-ethyl)-cyclohex-2-enone

Lösungsmittel

diethylether

acetonitril

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered
2. 2
   Sonstigeevaporated to dryness
3. 3
   Sonstigewas destined in vacuo (175° C., 0.01 mm Hg)
4. 4
   Sonstigeto give a slightly yellow oil which
5. 5
   SonstigeRecrystallization from isopropyl ether/isopropyl alcohol
6. 6
   Sonstigeyielded

Vorschrift

3-Vinyl-cyclohex-2-enone (0.75 g, 6.1 mmol) (prepared according to Nasarow's method) was dissolved in acetonitril (1 mL) and dipropylamine (1.5 g, 16 mmol) was added followed by Cs2CO3 (50 mg). After stirring the mixture at rt for 3 h it was diluted with diethylether (100 mL), filtered and evaporated to dryness. The residue was destined in vacuo (175° C., 0.01 mm Hg) to give a slightly yellow oil which was converted to the hydrochloride salt. Recrystallization from isopropyl ether/isopropyl alcohol yielded: 1.2 g, 4.6 mmol (75%), mp 95-97° C. IR (KBr) 2962, 2613, 1667; 1H-NMR (CDCl3) δ 5.84 (d, 1H), 2.65 (m, 2H), 2.27-2.60 (m, 9H), 1.99 (m, 2H), 1.39-1.51 (m, 5H), 0.86 (t, 6H) ppm; 13C-NMR (CDCl3) δ 198.2, 163.5, 124.9, 54.2, 50.1, 35.7, 33.7, 28.4, 21.2, 18.5, 10.4 ppm; MS (EI) m/z 223 (M+).

Quelle