Cyclohexanone → HCID 66618577, compound

HRID 2094195Notes

Reaction equation

HRID 2094195 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[C:8]1(=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C[Si]([C:19]#[N:20])(C)C>C(O)(=O)C>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:8]2([C:19]#[N:20])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:3]=1

Participants

5

Reactant 3

HCID 7967Cyclohexanone2×HCID 100093-Aminopyridine2×HCID 82115Trimethylsilyl cyanide

Product 1

HCID 66618577HCID 66618577, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1 g (10.6 mmol, 1.1 eq.) of 3-aminopyridine (starting material 1) is added to a solution of 1 ml (9.65 mmol, 1 eq.) of cyclohexanone (starting material 2) in 30 ml of acetic acid at 0° C. The solution is stirred for 15 minutes and 1.3 ml (9.75 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 until the pH is basic, and is extracted with dichloromethane. The organic phases are combined and washed with water. They are dried over sodium sulfate. The residue is chromatographed on silica gel (50/50 heptane/ethyl acetate and then ethyl acetate). 1-(Pyridin-3-ylamino)cyclohexanecarbonitrile is obtained in the form of white crystals.

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 until the pH
  3. extractionis extracted with dichloromethane
  4. washwashed with water
  5. dry with materialThey are dried over sodium sulfate
  6. customThe residue is chromatographed on silica gel (50/50 heptane/ethyl acetate

Sources & evidence

ORD record
ord-1e89080bc9eb4737bfbdfdb41a707f62
Source dataset
uspto-grants-2013_05
Patent number
US08445523B2

Reaction notes

Loading…