반응 #1747828

반응 방정식

NaBH3CN

KBr

NaHCO3

acetic acid

hydrochloride

3-(1-Propyl-1,4,5,6-tetrahydro-pyridin-3-yl)-cyclohex-2-enone

→

3-(1-Propyl-piperidin-3-yl)-cyclohex-2-enone

용매

water

THF

반응 조건

후처리

1. 1
   온도maintaining the temperature
2. 2
   workup.ADDITIONAfter the addition
3. 3
   기타at rt
4. 4
   기타overnight
5. 5
   추출followed by extraction with dichloromethane (5×50 mL)
6. 6
   건조The combined organic layers were dried (MgSO4)
7. 7
   기타evaporated
8. 8
   기타The residue was purified by column chromatography (silica, dichloromethane/ethanol 20:1)
9. 9
   기타to give a colorless oil which
10. 10
    기타Recrystallisation from isoprylether
11. 11
    기타gave 4.2 g, 17.5 mmol (77%), mp 184-185° C

실험 절차

3-(1-Propyl-1,4,5,6-tetrahydro-pyridin-3-yl)-cyclohex-2-enone (5.0 g, 22.8 mmol) (from b) above) was dissolved in THF (100 mL). At 0° C., acetic acid (1.38 mL, 22.8 mmol) was added followed by introduction of NaBH3CN (1.9 g, 30.0 mmol) in small portions maintaining the temperature. After the addition was complete the mixture was stirred for 1 h at this temperature and then at rt overnight. Work-up by addition of water (50 mL) and saturated aqueous NaHCO3 (50 mL) followed by extraction with dichloromethane (5×50 mL). The combined organic layers were dried (MgSO4) and evaporated. The residue was purified by column chromatography (silica, dichloromethane/ethanol 20:1) to give a colorless oil which was converted to the hydrochloride. Recrystallisation from isoprylether gave 4.2 g, 17.5 mmol (77%), mp 184-185° C. IR (KBr) 3396, 2941, 2469, 1667, 1455 cm−1; 1H-NMR (CDCl3) δ 5.83 (s, 1H), 3.85 (d, 2H), 2.29-2.56 (m, 7H), 1.23-2.17 (m, 10H), 0.88 (t, 3H) ppm; 13C-NMR (CDCl3) δ 198.4, 165.1, 123.4, 59.0, 55.6, 51.9, 41.6, 36.0, 27.3, 26.9, 22.8, 21.2, 17.6, 10.2 ppm; MS (EI) m/z 221 (M+).

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