Sodium Iodide → 1,3-Dihydro-3-(3-iodopropyl)-7,8-dimethoxy-2H-3-benzazepin-2-one

HRID 487559Notes

Reaction equation

HRID 487559 reaction equation
[CH3:1][O:2][C:3]1[C:18]([O:19][CH3:20])=[CH:17][C:6]2[CH2:7][C:8](=[O:16])[N:9]([CH2:12][CH2:13][CH2:14]Cl)[CH:10]=[CH:11][C:5]=2[CH:4]=1.[I-:21].[Na+]>CC(C)=O>[CH3:1][O:2][C:3]1[C:18]([O:19][CH3:20])=[CH:17][C:6]2[CH2:7][C:8](=[O:16])[N:9]([CH2:12][CH2:13][CH2:14][I:21])[CH:10]=[CH:11][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 130925033-(3-Chloropropyl)-1,3-dihydro-7,8-dimethoxy-2H-3-benzazepin-2-one

Product 1

HCID 190921901,3-Dihydro-3-(3-iodopropyl)-7,8-dimethoxy-2H-3-benzazepin-2-oneYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 12 g of 7,8-dimethoxy-3-[3-chloropropyl]-1,3-dihydro-2H-3-benzazepin-2-one obtained in accordance with the method described in the literature (Reiffer M. et al., J. Med. Chem. 1990; vol 33 (5): 1496-1504) and 6.2 g of sodium iodide in 50 cm3 of acetone are refluxed for 24 hours. After filtration and evaporation to dryness of the solvent, the residue is taken up in water and extracted with dichloromethane. The extract is separated off, dried over anhydrous magnesium sulphate and then concentrated in vacuo to yield 15.2 g of the desired compound.

Workup

  1. customobtained in accordance with the method
  2. temperatureare refluxed for 24 hours
  3. filtrationAfter filtration and evaporation to dryness of the solvent
  4. extractionextracted with dichloromethane
  5. customThe extract is separated off
  6. dry with materialdried over anhydrous magnesium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4701aedfd940499fa1ac32e91c2faba0
Source dataset
uspto-grants-1994_03
Patent number
US05296482

Reaction notes

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