Potassium Cyanide → HCID 22645388, compound

HRID 2414266Notes

Reaction equation

HRID 2414266 reaction equation
[CH2:1]([N:7]1[CH2:12][CH2:11][C:10]([CH3:27])([C:13]2[CH:18]=[CH:17][CH:16]=[C:15](OS(C(F)(F)F)(=O)=O)[CH:14]=2)[CH:9]([CH3:28])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C-:29]#[N:30].[K+]>CN1CCCC1=O>[NH3:7].[CH2:1]([N:7]1[CH2:12][CH2:11][C:10]([CH3:27])([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:29]#[N:30])[CH:14]=2)[CH:9]([CH3:28])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 22645393HCID 22645393, compound

Product 2

HCID 222AmmoniaHCID 22645388HCID 22645388, compoundYield 194.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 1-hexyl-3,4-dimethyl-4-(3-trifluoromethanesulfonyloxyphenyl)piperidine (Preparation 1, 500 mg, 1.19 mmol) in 1-methyl-2-pyrrolidinone (2.5 mL) was added to a flask containing potassium cyanide (155 mg, 2.38 mmol). The solution was de-oxygenated by evacuating and flushing with nitrogen three times. Catalytic quantities of palladium(II) acetate and 1,1 ′-bis(diphenylphosphino)ferrocene were added and the reaction mixture was warmed to 60° C., at which temperature it was stirred for 3 hours. The reaction mixture was cooled to room temperature and poured into saturated aqueous sodium hydrogencarbonate solution (50 mL). The product was extracted into ethyl acetate (3×30 mL). The combined organics were dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography on silica gel (15 g) eluted with a gradient of ethyl acetate:hexane:0.880 ammonia (20:79:1 to 50:49:1) to give the title compound as an oil (346 mg).

Workup

  1. customby evacuating
  2. customflushing with nitrogen three times
  3. additionCatalytic quantities of palladium(II) acetate and 1,1 ′-bis(diphenylphosphino)ferrocene were added
  4. temperatureThe reaction mixture was cooled to room temperature
  5. additionpoured into saturated aqueous sodium hydrogencarbonate solution (50 mL)
  6. extractionThe product was extracted into ethyl acetate (3×30 mL)
  7. dry with materialThe combined organics were dried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography on silica gel (15 g)
  10. washeluted with a gradient of ethyl acetate

Sources & evidence

ORD record
ord-8bb3ca434114462abb243744d87984c2
Source dataset
uspto-grants-2004_11
Patent number
US06812236B2

Reaction notes

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