Reaction #1747825

Reaction equation

3-Vinyl-cyclohex-2-enone

dipropylamine

KBr

Cs2CO3

→

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

Solvents

diethylether

acetonitril

Conditions

Workup

1. 1
   Filtrationfiltered
2. 2
   Otherevaporated to dryness
3. 3
   Otherwas destined in vacuo (175° C., 0.01 mm Hg)
4. 4
   Otherto give a slightly yellow oil which
5. 5
   OtherRecrystallization from isopropyl ether/isopropyl alcohol
6. 6
   Otheryielded

Procedure

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+).

Source