Propionitrile → HCID 58870174, compound

HRID 1667312Notes

Reaction equation

HRID 1667312 reaction equation
[C:1](#[N:4])[CH2:2][CH3:3].BrC1[CH:11]=[C:10](C)[C:9](/[CH:13]=[CH:14]/[CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)=[C:8]([CH3:28])[CH:7]=1.[C-]#N.[Na+]>[Cu](I)I.O>[C:1]([C:2]1[CH:7]=[C:8]([CH3:28])[C:9](/[CH:13]=[CH:14]/[CH:15]2[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20]2)=[C:10]([CH3:11])[CH:3]=1)#[N:4]

Participants

6

Reactant 3

HCID 7854PropionitrileHCID 8929Sodium CyanideHCID 9977921HCID 9977921, compound

Product 1

HCID 58870174HCID 58870174, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 962WaterSolvent

Procedure

Under argon atmosphere, 3 ml of propionitrile was added to a mixture of 339 mg of tert-butyl 4-[(E)-2-(4-bromo-2,6-dimethylphenyl)vinyl]piperidine-1-carboxylate, 89 mg of sodium cyanide, 53 mg of tetrakistriphenylphosphine palladium and 17 mg of copper iodide, followed by heating under reflux for 7 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 299 mg of tert-butyl 4-[(E)-2-(4-cyano-2,6-dimethylphenyl)vinyl]piperidine-1-carboxylate.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 7 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-9ec17c5979014a0e9123124cd85d5499
Source dataset
uspto-grants-2011_10
Patent number
US08044206B2

Reaction notes

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