Reacción #1747825

Ecuación de reacción

3-Vinyl-cyclohex-2-enone

dipropylamine

KBr

Cs2CO3

→

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

Disolventes

diethylether

acetonitril

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónfiltered
2. 2
   Otroevaporated to dryness
3. 3
   Otrowas destined in vacuo (175° C., 0.01 mm Hg)
4. 4
   Otroto give a slightly yellow oil which
5. 5
   OtroRecrystallization from isopropyl ether/isopropyl alcohol
6. 6
   Otroyielded

Procedimiento

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+).

Fuente