Benzaldehyde → HCID 712329, compound

HRID 244605Notes

Reaction equation

HRID 244605 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C:3](=[O:9])[CH2:2]2.[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Na+]>C(O)C>[CH:10](=[C:2]1/[N:1]2[CH2:8][CH2:7][CH:4]([C:3]/1=[O:9])[CH2:5][CH2:6]2)/[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 195073-Quinuclidinone

Product 1

HCID 712329HCID 712329, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-quinuclidinone (20.9 g, 167 mmol), benzaldehyde (17.7 g, 167 mmol), and one pellet of sodium hydroxide in 75 mL of ethanol was refluxed for 1.5 h. After the solution was cooled, the yellow precipitates were collected, washed with ethanol, and dried to give (Z)-2-benzylidenequinuclidin-3-one (32.5 g, yield: 91.2%, mp 130-132° C.).

Workup

  1. temperaturewas refluxed for 1.5 h
  2. temperatureAfter the solution was cooled
  3. customthe yellow precipitates
  4. customwere collected
  5. washwashed with ethanol
  6. customdried

Sources & evidence

ORD record
ord-227faeb458dd42ff8860133bc0e10f3c
Source dataset
uspto-grants-2014_02
Patent number
US08658669B2

Reaction notes

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