Acetic Acid → HCID 66618616, compound

HRID 2094201Notes

Reaction equation

HRID 2094201 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5](OC)=[N:6][CH:7]=1.[C:10]1(=O)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C[Si]([C:21]#[N:22])(C)C.[C:23](O)(=O)C>>[CH3:23][C:5]1[N:6]=[CH:7][C:2]([NH:1][C:10]2([C:21]#[N:22])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:3][CH:4]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 7967Cyclohexanone2×HCID 811216-Methoxy-3-pyridinylamine2×HCID 82115Trimethylsilyl cyanide

Product 1

HCID 66618616HCID 66618616, compound

Procedure

10 g (92.5 mmol, 1 eq.) of 6-methylpyridin-3-ylamine (starting material 1) are added to a solution of 9.6 ml (92.6 mmol, 1 eq.) of cyclohexanone (starting material 2) in 100 ml of acetic acid at 0° C. The solution is stirred for 15 minutes, and 12.4 ml (93 mmol, 1 eq.) of trimethylsilyl cyanide are added. The reaction medium is stirred for 24 hours at room temperature. It is then poured gently into ice-cold ammonium hydroxide solution and extracted with ethyl acetate. The organic phases are combined and washed with water. They are dried over sodium sulfate. The residue is filtered off on silica, which is then washed with ethyl acetate. After concentrating under vacuum, 1-(6-methylpyridin-3-ylamino)cyclohexanecarbonitrile is obtained in the form of a white solid.

Workup

  1. stirringThe reaction medium is stirred for 24 hours at room temperature
  2. additionIt is then poured gently into ice-cold ammonium hydroxide solution
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. dry with materialThey are dried over sodium sulfate
  6. filtrationThe residue is filtered off on silica, which
  7. washis then washed with ethyl acetate
  8. concentrationAfter concentrating under vacuum

Sources & evidence

ORD record
ord-362ce80daebe436fa660ae32631d61a6
Source dataset
uspto-grants-2013_05
Patent number
US08445523B2

Reaction notes

Loading…