Glutaraldehyde → 9-Benzyl-9-azabicyclo[3.3.1]nonan-3-one

HRID 1939969Notes

Reaction equation

HRID 1939969 reaction equation
[CH:1](=O)[CH2:2][CH2:3][CH2:4][CH:5]=[O:6].[CH2:8]([C:15](O)=O)[C:9](CC(O)=O)=O.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>Cl>[CH2:18]([N:25]1[CH:3]2[CH2:2][CH2:1][CH2:15][CH:8]1[CH2:9][C:5](=[O:6])[CH2:4]2)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 3485GlutaraldehydeHCID 7504BenzylamineHCID 68328Acetonedicarboxylic acid

Product 1

HCID 4195319-Benzyl-9-azabicyclo[3.3.1]nonan-3-oneYield 33%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a 1 L round-bottomed flask equipped with a condenser and nitrogen inlet were added 80 g (0.2 mol) of a 25% aqueous solution of glutaraldehyde, 29.2 g (0.2 mol) 1,3-acetonedicarboxylic acid, and 11.4 g (0.2 mol) benzylamine. After the initial reaction had subsided, the pH was adjusted to 5 and maintained for 14 hours. The reaction was then taken up in 6N HCl, washed with ethyl acetate, and basified with 6N sodium hydroxide solution. The aqueous layer was extracted with methylene chloride, and the organic layer filtered through diatomaceous earth (Celite [trademark]) and evaporated. The residue was chromatographed on silica gel with ethyl acetate/methylene chloride as eluent to afford 15.034 g (33%) of a pale orange solid, mp 70-73C.

Workup

  1. customTo a 1 L round-bottomed flask equipped with a condenser and nitrogen inlet
  2. customAfter the initial reaction
  3. temperaturemaintained for 14 hours
  4. washwashed with ethyl acetate
  5. extractionThe aqueous layer was extracted with methylene chloride
  6. filtrationthe organic layer filtered through diatomaceous earth (Celite [trademark])
  7. customevaporated
  8. customThe residue was chromatographed on silica gel with ethyl acetate/methylene chloride as eluent

Sources & evidence

ORD record
ord-12e97f8d13e14c29a41a8f782b518aef
Source dataset
uspto-grants-1997_12
Patent number
US05698568

Reaction notes

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