Sodium Iodide → HCID 53712839, compound

HRID 2400020Notes

Reaction equation

HRID 2400020 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[NH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.Br[CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][C:27]([O:29][CH3:30])=[O:28]>C(#N)C>[N:9]1([CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 10589341HCID 10589341, compound

Product 1

HCID 53712839HCID 53712839, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.51 g of potassium carbonate, 0.3 g of sodium iodide and then 1.0 cm3 of piperidine are successively added to a solution of 2.87 g of methyl [2-(3-bromopropoxy)-phenyl]acetate in 30 cm3 of acetonitrile. The reaction mixture is refluxed for 2 hours and then filtered. The filtrate is concentrated to dryness and the residue obtained is chromatographed on a silica gel column (particle size 0.04-0.06 mm, diameter 4 cm, height 50 cm), eluting under a nitrogen pressure of 0.1 bar with an ethyl acetate and methanol mixture (80/20 by volume) and collecting fractions of 125 cm3. Fractions 9 to 16 are pooled and concentrated to dryness. The residue is triturated in diisopropyl oxide, the suspension is filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). 2.0 g of methyl [2-(3-piperidinopropoxy)phenyl]-acetate are obtained in the form of a yellow oil which is used as it in the next stage.

Workup

  1. temperatureThe reaction mixture is refluxed for 2 hours
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated to dryness
  4. customthe residue obtained
  5. customis chromatographed on a silica gel column (particle size 0.04-0.06 mm, diameter 4 cm, height 50 cm)
  6. washeluting under a nitrogen pressure of 0.1 bar with an ethyl acetate and methanol mixture (80/20 by volume)
  7. customcollecting fractions of 125 cm3
  8. concentrationconcentrated to dryness
  9. customThe residue is triturated in diisopropyl oxide
  10. filtrationthe suspension is filtered
  11. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-ea20656a2dc948699a80b42fde2f66e7
Source dataset
uspto-grants-1995_09
Patent number
US05451601

Reaction notes

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