Sodium Hydroxide → HCID 59187101, compound

HRID 408632Notes

Reaction equation

HRID 408632 reaction equation
[N:1]12[CH2:9][C:5]([C:10]3[CH:11]=[CH:12][C:13](O)=[N:14][CH:15]=3)([CH2:6][CH2:7][CH2:8]1)[CH2:4][CH2:3][CH2:2]2.P(Cl)(Cl)([Cl:19])=O.[OH-].[Na+]>>[Cl:19][C:13]1[N:14]=[CH:15][C:10]([C:5]23[CH2:9][N:1]([CH2:8][CH2:7][CH2:6]2)[CH2:2][CH2:3][CH2:4]3)=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178515823HCID 178515823, compound

Product 1

HCID 59187101HCID 59187101, compoundYield 42.4%

Conditions

Temperature
140 °C

Procedure

1 g (4.59 mmol) of 5-(1-azabicyclo[3.3.1]non-5-yl)pyridin-2-ol obtained in Example 1, in solution in 12.8 mol (137.7 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 461 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-9b49e609221642deb862b09c134ac571
Source dataset
uspto-grants-2014_06
Patent number
US08759343B2

Reaction notes

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