Cyclohexanone → HCID 66618552, compound

HRID 2094199Notes

Reaction equation

HRID 2094199 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[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(O)(=O)C>[CH3:9][O:8][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 3

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

Product 1

HCID 66618552HCID 66618552, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5 g (40.3 mmol, 1 eq.) of 5-amino-2-methoxypyridine (starting material 1) are added to a solution of 4.2 ml (40.5 mmol, 1 eq.) of cyclohexanone (starting material 2) in 20 ml of acetic acid at 0° C. The solution is stirred for 15 minutes, and 5.4 ml (40.5 mmol, 1 eq.) of trimethylsilyl cyanide are added. The reaction medium is stirred for 2 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 precipitated from dichloromethane and heptane. 1-(6-Methoxypyridin-3-ylamino)-cyclohexanecarbonitrile is obtained in the form of a pink-coloured solid.

Workup

  1. stirringThe reaction medium is stirred for 2 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. customThe residue is precipitated from dichloromethane and heptane

Sources & evidence

ORD record
ord-03377853a2724bba85eb667dfc4455ec
Source dataset
uspto-grants-2013_05
Patent number
US08445523B2

Reaction notes

Loading…