Potassium Iodide → HCID 23004143, compound

HRID 382662Notes

Reaction equation

HRID 382662 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:14][CH2:15][CH2:16][C:17]#[N:18].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(O)CCC.O1CCOCC1>[C:1]1([CH:7]2[CH2:8][CH2:9][N:10]([CH2:14][CH2:15][CH2:16][C:17]#[N:18])[CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 214124-BromobutyronitrileHCID 698734-Phenylpiperidine

Product 1

HCID 23004143HCID 23004143, compoundYield 53.7%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 4-phenylpiperidine (5.20 g, 32.2 mmol, 1.00 equiv), 4-bromobutyronitrile (4.81 mL, 48.4 mmol, 1.50 equiv), potassium carbonate (11.14 g, 80.6 mmol, 2.50 equiv), and potassium iodide (266 mg, 12.9 mmol, 0.4 equiv) in n-butanol (60 mL) and 1,4-dioxane (60 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, MeOH-EtoAc 1:19) to afford 3.95 g of 4-(4-phenylpiperidin-1-yl)butyronitrile (white solid, 53%), which was characterized spectroscopically.

Workup

  1. temperatureat reflux under argon for 48 hours
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography (SiO2, MeOH-EtoAc 1:19)

Sources & evidence

ORD record
ord-0f404e48424e48a0afb26c65338b07f0
Source dataset
uspto-grants-2001_10
Patent number
US06310076B1

Reaction notes

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