反応 #1747825

反応方程式

3-Vinyl-cyclohex-2-enone

dipropylamine

KBr

Cs2CO3

→

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

溶媒

diethylether

acetonitril

反応条件

後処理

1. 1
   ろ過filtered
2. 2
   その他evaporated to dryness
3. 3
   その他was destined in vacuo (175° C., 0.01 mm Hg)
4. 4
   その他to give a slightly yellow oil which
5. 5
   その他Recrystallization from isopropyl ether/isopropyl alcohol
6. 6
   その他yielded

実験手順

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+).

出典