Sodium Iodide → HCID 59822101, compound

HRID 564047Notes

Reaction equation

HRID 564047 reaction equation
Cl[CH2:2][CH2:3][C:4]1[CH:20]=[CH:19][C:7]2[CH2:8][CH2:9][N:10]([C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH2:11][CH2:12][C:6]=2[CH:5]=1.[I-:21].[Na+]>CC(C)=O>[F:15][C:14]([F:17])([F:16])[C:13]([N:10]1[CH2:9][CH2:8][C:7]2[CH:19]=[CH:20][C:4]([CH2:3][CH2:2][I:21])=[CH:5][C:6]=2[CH2:12][CH2:11]1)=[O:18]

Participants

4

Reactant 2

HCID 5238Sodium Iodide2×HCID 86623683HCID 86623683, compound

Product 1

HCID 59822101HCID 59822101, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 800 mg (2.62 mmol) 1-[7-(2-chloro-ethyl)-1,2,4,5-tetrahydro-3-benzazepin-3-yl]-2,2,2-trifluoro-ethanone (preparation 6a) in 40 mL acetone is added 471 mg (3.14 mmol) sodium iodide. The reaction mixture is refluxed overnight, excess sodium iodide is added and the reaction mixture is refluxed additional three days. The solvent is evaporated, the residue is diluted with EtOAc and washed twice with water. The organic phase is dried over MgSO4, filtered and the solvent is evaporated. The residue is purified via reverse HPLC chromatography (Zorbax stable bond; C18; water (0.1% formic acid)/acetonitrile (0.1% formic acid) 95:5 to 10:90).

Workup

  1. temperatureThe reaction mixture is refluxed overnight
  2. temperaturethe reaction mixture is refluxed additional three days
  3. customThe solvent is evaporated
  4. additionthe residue is diluted with EtOAc
  5. washwashed twice with water
  6. dry with materialThe organic phase is dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent is evaporated
  9. customThe residue is purified via reverse HPLC chromatography (Zorbax stable bond; C18; water (0.1% formic acid)/acetonitrile (0.1% formic acid) 95:5 to 10:90)

Sources & evidence

ORD record
ord-c02adfc349884c7b8ae5ed1481ad530e
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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