Sodium Iodide → 2,3,4,5-tetrahydro-1H-1-benzazepine

HRID 1440276Notes

Reaction equation

HRID 1440276 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:11](C(=O)C3C=CC(NC(=O)C4C=CC=CC=4OCCOS(C)(=O)=O)=NC=3)[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:37]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].C(NC1CCNCC1)(=O)C>CN(C)C=O.O>[NH:11]1[C:5]2[CH:4]=[CH:3][CH:2]=[CH:37][C:6]=2[CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 14451564-AcetamidopiperidineHCID 22903480HCID 22903480, compound

Product 1

HCID 5765032,3,4,5-tetrahydro-1H-1-benzazepineYield 184.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 7-chloro-1-{6-[2-(2-methanesulfonyloxyethoxy)-benzoylamino]nicotinoyl}-2,3,4,5-tetrahydro-1H-benzazepine (0.6 g) in dimethylformamide (5 ml) are added sodium iodide (0.22 g), potassium carbonate (0.23 g) and 4-acetylaminopiperidine (0.2 g), and the mixture is heated with stirring at 110° C. for 2 hours. The mixture is cooled, and thereto is added water, and the mixture is extracted with dichloromethane. The extract is washed with water, dried over magnesium sulfate, and evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography to give 7-chloro-1-{6-[2-(4-acetylamino-1-piperidinyl)-ethoxy]benzoylamino]nicotinoyl}-2,3,4,5-tetrahydro-1H-benzazepine (0.3 g) as white powder.

Workup

  1. temperaturethe mixture is heated
  2. temperatureThe mixture is cooled
  3. extractionthe mixture is extracted with dichloromethane
  4. washThe extract is washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customto remove the solvent
  8. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-22588a4616cd45719b216d638d130157
Source dataset
uspto-grants-1996_03
Patent number
US05498609

Reaction notes

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