Sodium Iodide → HCID 19608252, compound

HRID 745063Notes

Reaction equation

HRID 745063 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:24]=[CH:23][C:9]([C:10]([N:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])=[CH:8][CH:7]=1)=[O:4].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH:33]1([NH2:39])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>CN(C)C=O>[CH:33]1([NH:39][CH2:2][C:3]([NH:5][C:6]2[CH:24]=[CH:23][C:9]([C:10]([N:12]3[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[CH2:16][CH2:15][CH2:14][CH2:13]3)=[O:11])=[CH:8][CH:7]=2)=[O:4])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7965CyclohexylamineHCID 11430Potassium CarbonateHCID 19608248HCID 19608248, compound

Product 1

HCID 19608252HCID 19608252, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[4-(2-chloroacetylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (2.06 g) in dimethylformamide (5 ml) are added sodium iodide (0.90 g), potassium carbonate (1.1 g) and cyclohexylamine (0.89 g), and the mixture is stirred at room temperature for 2 hours. Dimethylformamide is distilled off under reduced pressure and water is added to the resulting residue. The mixture is extracted with dichloromethane. The organic layer is washed successively with water and saturated saline solution, and dried over magnesium sulfate. The solvent is distilled off under reduced pressure and the resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate), and recrystallized from n-hexane/ethyl acetate to give 1-[4-(2-cyclohexylaminoacetylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (2.03 g) as white powder, m.p. 139°-142° C.

Workup

  1. distillationDimethylformamide is distilled off under reduced pressure and water
  2. additionis added to the resulting residue
  3. extractionThe mixture is extracted with dichloromethane
  4. washThe organic layer is washed successively with water and saturated saline solution
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent is distilled off under reduced pressure
  7. customthe resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate)
  8. customrecrystallized from n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-34c21caf3ca047bfb720b33b825a3cfc
Source dataset
uspto-grants-1996_09
Patent number
US05559230

Reaction notes

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