تفاعل #1747828

معادلة التفاعل

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

المذيبات

water

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةmaintaining the temperature
2. 2
   workup.ADDITIONAfter the addition
3. 3
   أخرىat rt
4. 4
   أخرىovernight
5. 5
   استخلاصfollowed by extraction with dichloromethane (5×50 mL)
6. 6
   تجفيفThe combined organic layers were dried (MgSO4)
7. 7
   أخرىevaporated
8. 8
   أخرىThe residue was purified by column chromatography (silica, dichloromethane/ethanol 20:1)
9. 9
   أخرىto give a colorless oil which
10. 10
    أخرىRecrystallisation from isoprylether
11. 11
    أخرىgave 4.2 g, 17.5 mmol (77%), mp 184-185° C

الإجراء التجريبي

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+).

المصدر