Potassium Iodide → (4,4-Diphenylpiperidin-1-yl)acetonitrile

HRID 964221Notes

Reaction equation

HRID 964221 reaction equation
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:20][C:21]#[N:22].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(O)CCC.O1CCOCC1>[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:8][CH2:9][N:10]([CH2:20][C:21]#[N:22])[CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 28232394,4-Diphenylpiperidine

Product 1

HCID 23004060(4,4-Diphenylpiperidin-1-yl)acetonitrileYield 86%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 4,4-diphenylpiperidine (4.00 g, 16.9 mmol, 1.00 equiv), chloroacetonitrile (1.40 mL, 21.9 mmol, 1.30 equiv, Aldrich), potassium carbonate (4.67 g, 33.8 mmol, 2.00 equiv), and potassium iodide (561 mg, 3.38 mmol, 0.20 equiv) in n-butanol (20 mL) and 1,4-dioxane (20 mL) was stirred at reflux under argon for 48 hours. The mixture was cooled to room temperature and concentrated. The residue was purified by flash chromatography (SiO2, EtOAc) to afford 4.01 g (86%) of white solid, which was characterized spectroscopically.

Workup

  1. temperatureat reflux under argon for 48 hours
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography (SiO2, EtOAc)

Sources & evidence

ORD record
ord-2e49541c2fb0417d8ab3b4a5e35089b8
Source dataset
uspto-grants-1998_06
Patent number
US05767131

Reaction notes

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