Pyridine → HCID 19004165, compound

HRID 2225375Notes

Reaction equation

HRID 2225375 reaction equation
[CH2:1]([N:8]1[CH2:15][CH:14]2[N:16]([CH3:17])[CH:10]([CH2:11][C:12](=O)[CH2:13]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:20][OH:21].N1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>O.C(O)C>[CH2:1]([N:8]1[CH2:15][CH:14]2[N:16]([CH3:17])[CH:10]([CH2:11][C:12](=[N:20][OH:21])[CH2:13]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 19004159HCID 19004159, compound

Product 1

HCID 19004165HCID 19004165, compoundYield 878.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3-benzyl-9-methyl-7-oxo-3,9-diazabicyclo[3.3.1]nonane (9.33 g ), hydroxylamine hydrochloride (3.98 g ), pyridine (12.5 ml ) and ethanol was heated at reflux for 2 hrs. The reaction solution was cooled down to room temperature, potassium carbonate (15 g) and water (8 ml ) were added and the stirring was continued for a while. The resultant suspension was filtered through celite and the solvent was distilled off under reduced pressure. The resulting residue was mixed with chloroform (200 ml ) and filtered through Celite. The solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography and crystallized to afford the title compound (3. 87 g ).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hrs
  3. filtrationThe resultant suspension was filtered through celite
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionThe resulting residue was mixed with chloroform (200 ml )
  6. filtrationfiltered through Celite
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe resultant residue was purified by silica gel column chromatography
  9. customcrystallized

Sources & evidence

ORD record
ord-f86028de3e474330857390e54f9da737
Source dataset
uspto-grants-1994_09
Patent number
US05344831

Reaction notes

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