Isopropyl iodide → HCID 19772016, compound

HRID 1614608Notes

Reaction equation

HRID 1614608 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[CH:16](I)([CH3:18])[CH3:17].C(=O)(O)[O-].[Na+]>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH:16]([CH3:18])[CH3:17])[CH2:10][CH2:9]2)=[O:7])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 516892Sodium BicarbonateHCID 27244404-(4-Fluorobenzoyl)piperidine

Product 1

HCID 19772016HCID 19772016, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 34.16 g (0.165 mol) of the 4-(4-fluorobenzoyl)piperidine, 33.80 g (0.199 mol) of isopropyl iodide and excessive sodium bicarbonate in 600 mL of acetonitrile was heated at reflux for 14 h. The solvent was removed in vacuo, and the residue was partitioned between CH2Cl2 and dilute NaOH. The CH2Cl2 solution was dried (Na2SO4), and the solvent was removed in vacuo to give a solid. This was recrystallized from CH2Cl2 /hexane to give 31.89 g (77.6%) of crystalline solid, mp 120°-121° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 14 h
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between CH2Cl2 and dilute NaOH
  5. dry with materialThe CH2Cl2 solution was dried (Na2SO4)
  6. customthe solvent was removed in vacuo
  7. customto give a solid
  8. customThis was recrystallized from CH2Cl2 /hexane

Sources & evidence

ORD record
ord-c6d468b354284419965323ef4780a6a9
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

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