Sodium Iodide → HCID 11959535, compound

HRID 1947268Notes

Reaction equation

HRID 1947268 reaction equation
O.[NH:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[I:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1>C(#N)C>[I:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][N:2]2[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 9542584-Iodobenzyl bromideHCID 21584170Piperidin-4-one hydrate

Product 1

HCID 11959535HCID 11959535, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 3 L flask was charged with 4-piperidinone hydrate (10.4 g, 60.8 mmol), K2CO3 (45 g, 326 mmol), acetonitrile (2000 mL) and NaI (0.49 g, 3.3 mmol). To the mixture while stirring was added 4-iodobenzyl bromide (17.5 g, 58.8 mmol). The mixture was stirred at rt overnight, filtered over a coarse glass frit and the filtrate concentrated to give 25 g crude. Recrystallization from hot EtOAc in hexanes gave 11 g (53%) of a clean crop as orange crystals: LRMS (M+1)=316.

Workup

  1. stirringThe mixture was stirred at rt overnight
  2. filtrationfiltered over a coarse glass frit
  3. concentrationthe filtrate concentrated
  4. customto give 25 g crude
  5. customRecrystallization from hot EtOAc in hexanes
  6. customgave 11 g (53%) of a clean crop as orange crystals

Sources & evidence

ORD record
ord-0db09cd4846c4e53bba335d76c1c2760
Source dataset
uspto-grants-2013_03
Patent number
US08399473B2

Reaction notes

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