Benzaldehyde → HCID 59904499, compound

HRID 2303339Notes

Reaction equation

HRID 2303339 reaction equation
[OH-].[Na+].[CH2:3]([N:10]1[CH:15]2[CH2:16][CH2:17][CH:11]1[C:12](=[O:18])[CH2:13][CH2:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[CH2:3]([N:10]1[CH:15]2[CH2:16][CH2:17][CH:11]1[C:12](=[O:18])[C:13](=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:14]2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 18461084HCID 18461084, compound

Product 1

HCID 59904499HCID 59904499, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 5N sodium hydroxide solution (1.62 mL, 0.5 equiv.) was added to (±)-8-benzyl-8-aza-bicyclo[3.2.1]octan-2-one (3.49 g, 16.2 mmol), followed by a solution of benzaldehyde (2.59 mL, 2.69 g, 16.2 mmol) in ethanol (160 mL). The solution was stirred at ambient temperature for 4.5 h. The solution was concentrated under reduced pressure, and the residue was taken up in dichloromethane (160 mL). The mixture was washed with water (160 mL) and brine (160 mL), dried (sodium sulfate), filtered, and the solvent evaporated under reduced pressure to give crude product (4.96 g, theoretical yield 4.92 g) as an orange oil.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. washThe mixture was washed with water (160 mL) and brine (160 mL)
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-e70716fa5fbc43f69c7b3a7065d83a3e
Source dataset
uspto-grants-2002_08
Patent number
US06432976B1

Reaction notes

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