Iodine → HCID 67491521, compound

HRID 2167749Notes

Reaction equation

HRID 2167749 reaction equation
[CH2:1]([O:3][N:4]1[C:9]([CH3:11])([CH3:10])[CH2:8][C:7](=[O:12])[CH2:6][C:5]1([CH3:14])[CH3:13])[CH3:2].[CH3:15][Si:16](C#N)([CH3:18])[CH3:17].II.[C:23](#[N:25])C>CCCCCC.C(OCC)(=O)C>[CH2:1]([O:3][N:4]1[C:5]([CH3:13])([CH3:14])[CH2:6][C:7]([C:23]#[N:25])([O:12][Si:16]([CH3:18])([CH3:17])[CH3:15])[CH2:8][C:9]1([CH3:11])[CH3:10])[CH3:2]

Participants

6

Reactant 4

HCID 807IodineHCID 6342AcetonitrileHCID 82115Trimethylsilyl cyanideHCID 21348356HCID 21348356, compound

Product 1

HCID 67491521HCID 67491521, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of 0.398 g (2 mmol) 1-ethoxy-2,2,6,6-tetramethyl-piperidin-4-one in dry acetonitrile is added 0.297 g (3 mmol) trimethylsilyl cyanide and a catalytic amount of iodine. The solution is stirred at rt over night. The reaction mixture is extracted with ethyl acetate, washed with Na2CO3 solution and brine. The organic layer is separated, dried over Na2SO4, filtered and the solvent is removed under reduced pressure. A yellow oil was obtained and subsequently subjected to flash chromatography on silica gel using 4:1 hexane/ethyl acetate as eluent. The product was obtained as a pale yellow oil.

Workup

  1. extractionThe reaction mixture is extracted with ethyl acetate
  2. washwashed with Na2CO3 solution and brine
  3. customThe organic layer is separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent is removed under reduced pressure
  7. customA yellow oil was obtained
  8. customThe product was obtained as a pale yellow oil

Sources & evidence

ORD record
ord-454a91bde92643fa9bd4a11734581294
Source dataset
uspto-grants-2015_06
Patent number
US09045480B2

Reaction notes

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