Benzaldehyde → 2-Benzylidene-3-quinuclidinone

HRID 1656913Notes

Reaction equation

HRID 1656913 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=[O:10])[CH2:3]2.[OH-].[Na+].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O.C(O)C>[CH:13](=[C:3]1[C:4](=[O:10])[CH:5]2[CH2:8][CH2:9][N:2]1[CH2:7][CH2:6]2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 14798Sodium Hydroxide2×HCID 1020191-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1)

Product 1

HCID 2433762-Benzylidene-3-quinuclidinone

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To quinuclidine-3-one hydrochloride (Aldrich Chemical Co.) (49.9 g) in water (200 ml) was added sodium hydroxide (12.5 g, 0.310 mol). The aqueous layer was extracted with dichloromethane (2×200 ml) and the combined organic layers dired (Na2CO3), filtered, and evaporated in vacuo to give a colourless oil. The oil (38.64 g) was dissolved in ethanol (400 ml) and sodium hydroxide (3 g) added, followed by benzaldehyde (32.8 g). The reaction mixture was heated at reflux for 2 h. On cooling the product crystallized from the solution as a yellow solid. 1H NMR (CDCl3) δ 1.96-2.08 (4H, m), 2.62-2.66 (1H, m), 2.92-3.24 (4H, m), 7.02 (1H, s), 7.32-7.42 (3H, m), 8.00-8.04 (2H, m).

Workup

  1. extractionThe aqueous layer was extracted with dichloromethane (2×200 ml)
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. customto give a colourless oil
  5. temperatureThe reaction mixture was heated
  6. temperatureat reflux for 2 h
  7. temperatureOn cooling the product
  8. customcrystallized from the solution as a yellow solid

Sources & evidence

ORD record
ord-228169fb075b4d07936932231d8917e6
Source dataset
uspto-grants-1993_10
Patent number
US05256671

Reaction notes

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