Sodium Hydroxide → HCID 66618594, compound

HRID 2094196Notes

Reaction equation

HRID 2094196 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]2([C:14]#[N:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:2]=1.[OH-:16].[Na+]>S(=O)(=O)(O)O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]2([C:14]([NH2:15])=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66618577HCID 66618577, compound

Product 1

HCID 66618594HCID 66618594, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

1.23 g (6.11 mmol) of 1-(pyridin-3-ylamino)-cyclohexanecarbonitrile are dissolved in 20 ml of concentrated sulfuric acid. The reaction medium is stirred at room temperature for 72 hours. It is then poured slowly into ice and the pH is brought to 14 with sodium hydroxide, and extracted with dichloromethane. The organic phases are combined and washed with water. They are dried over sodium sulfate. The solvents are evaporated off. The residue is chromatographed on silica gel (ethyl acetate and then 90/10 ethyl acetate/methanol). 1-(Pyridin-3-ylamino)-cyclohexanecarboxylic acid amide is obtained in the form of a white solid.

Workup

  1. additionIt is then poured slowly into ice
  2. extractionextracted with dichloromethane
  3. washwashed with water
  4. dry with materialThey are dried over sodium sulfate
  5. customThe solvents are evaporated off
  6. customThe residue is chromatographed on silica gel (ethyl acetate

Sources & evidence

ORD record
ord-9bbd9b097ccd48988f9854b78dc9bbd5
Source dataset
uspto-grants-2013_05
Patent number
US08445523B2

Reaction notes

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