Реакция #1747828

Уравнение реакции

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

Растворители

water

THF

Условия реакции

Обработка

1. 1
   Температураmaintaining the temperature
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Другоеat rt
4. 4
   Другоеovernight
5. 5
   Экстракцияfollowed by extraction with dichloromethane (5×50 mL)
6. 6
   СушкаThe combined organic layers were dried (MgSO4)
7. 7
   Другоеevaporated
8. 8
   ДругоеThe residue was purified by column chromatography (silica, dichloromethane/ethanol 20:1)
9. 9
   Другоеto give a colorless oil which
10. 10
    ДругоеRecrystallisation from isoprylether
11. 11
    Другоеgave 4.2 g, 17.5 mmol (77%), mp 184-185° C

Методика

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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