Sodium Hydroxide → HCID 59187099, compound

HRID 408637Notes

Reaction equation

HRID 408637 reaction equation
[N:1]12[CH2:7][C:4]([C:8]3[CH:9]=[CH:10][C:11](O)=[N:12][CH:13]=3)([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.P(Cl)(Cl)([Cl:17])=O.[OH-].[Na+]>>[Cl:17][C:11]1[N:12]=[CH:13][C:8]([C:4]23[CH2:7][N:1]([CH2:6][CH2:5]2)[CH2:2][CH2:3]3)=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178515824HCID 178515824, compound

Product 1

HCID 59187099HCID 59187099, compoundYield 91.4%

Conditions

Temperature
140 °C

Procedure

0.37 g (1.94 mmol) of 5-(1-azabicyclo[2.2.1]hept-4-yl)pyridin-2-ol obtained in Example 4, in solution in 5.44 ml (58.35 mmol) of phosphorus oxychloride, is introduced into a sealed tube and the combined mixture is subsequently stirred at 140° C. for 45 minutes. The reaction mixture is subsequently brought back to ambient temperature, poured onto 200 g of crushed ice and stirred for 15 minutes. The medium is then very slowly adjusted to pH 10 with a concentrated sodium hydroxide solution. The combined mixture is subsequently extracted twice with chloroform and the organic phases are subsequently combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to provide 370 mg of the desired compound in the form of a brown powder.

Workup

  1. customis subsequently brought back to ambient temperature
  2. stirringstirred for 15 minutes
  3. extractionThe combined mixture is subsequently extracted twice with chloroform
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1dfbc4390b3644df9189b6dc809458da
Source dataset
uspto-grants-2014_06
Patent number
US08759343B2

Reaction notes

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