Sodium Iodide → HCID 59865001, compound

HRID 1669731Notes

Reaction equation

HRID 1669731 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][CH:7]=1.[CH3:13][C:14]1([CH3:20])[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[I:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:16]2[CH2:17][CH2:18][CH2:19][C:14]([CH3:20])([CH3:13])[CH2:15]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 709423,3-DimethylpiperidineHCID 158955201-(3-Chloropropoxy)-4-iodobenzene2×

Product 1

HCID 59865001HCID 59865001, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-[(3-chloropropyl)oxy]-4-iodobenzene (for example, as prepared for Intermediate 1) (6.5 g, 20 mmol), 3,3-dimethyl piperidine (commercially available, for example from Alfa) (3.39 g, 30 mmol), sodium iodide (2.99 g, 20 mmol) and potassium carbonate (3.3 g, 20 mmol) in anhydrous acetonitrile (100 ml) was heated at reflux overnight. The mixture was allowed to cool to room temperature, evaporated to dryness and quenched with water and extracted with dichloromethane, dried, filtered and concentrated to afford the title compound (8 g). LCMS RT=2.37 min, ES+ve m/z 374 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customevaporated to dryness
  4. customquenched with water
  5. extractionextracted with dichloromethane
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9d75581846864b9d9bfb54712e34e90a
Source dataset
uspto-grants-2011_08
Patent number
US07989629B2

Reaction notes

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