Benzaldehyde → 2-(Phenylmethylene)-1-azabicyclo[2.2.1]heptan-3-one

HRID 1735792Notes

Reaction equation

HRID 1735792 reaction equation
[N:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[C:3](=[O:8])[CH2:2]2.[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[Na+]>C(O)C>[C:10]1([CH:9]=[C:2]2[C:3](=[O:8])[CH:4]3[CH2:7][N:1]2[CH2:6][CH2:5]3)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 108554071-Azabicyclo[2.2.1]heptan-3-one

Product 1

HCID 540693242-(Phenylmethylene)-1-azabicyclo[2.2.1]heptan-3-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-azabicyclo[2.2.1]heptan-3-one (2.65g), benzaldehyde (3.64 ml) and sodium hydroxide (1.15 g) in ethanol (25 ml) was heated at reflux for 40 min. After cooling the solvent was removed in vacuo and the residue partitioned between dichloromethane (300 ml) and water (300 ml). The aqueous layer was further extracted with dichloromethane (2×300 ml). The organic extracts were combined, backwashed with brine (100 ml), dried and concentrated in vacuo to give an orange oil (5.84 g). The oil was purified by FCC, using gradient elution with petrol/ethyl acetate 6:1 to 3:1 to give the title compound as a yellow solid (3.80 g). m.p. 61°-63°. TLC (petrol/ethyl acetate, 3:1) Rf 0.39.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 40 min
  3. temperatureAfter cooling the solvent
  4. customwas removed in vacuo
  5. customthe residue partitioned between dichloromethane (300 ml) and water (300 ml)
  6. extractionThe aqueous layer was further extracted with dichloromethane (2×300 ml)
  7. customdried
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cdfe8f94752f499592e4043b6eab6f86
Source dataset
uspto-grants-1996_07
Patent number
US05538982

Reaction notes

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