반응 #1747825

반응 방정식

3-Vinyl-cyclohex-2-enone

dipropylamine

KBr

Cs2CO3

→

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

용매

diethylether

acetonitril

반응 조건

후처리

1. 1
   여과filtered
2. 2
   기타evaporated to dryness
3. 3
   기타was destined in vacuo (175° C., 0.01 mm Hg)
4. 4
   기타to give a slightly yellow oil which
5. 5
   기타Recrystallization from isopropyl ether/isopropyl alcohol
6. 6
   기타yielded

실험 절차

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+).

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