Sodium Iodide → HCID 19608252, compound

HRID 1603103Notes

Reaction equation

HRID 1603103 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-7f483652973447828f0835f768de8f9e
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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