Sodium Iodide → 7-chloro-1-(2-methyl-4-(2-methylbenzamido)benzoyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl 4-(4-acetylpiperazin-1-yl)butyrate

HRID 1626034Notes

Reaction equation

HRID 1626034 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15](=[O:33])[C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:31])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[CH3:30])=[CH:18][C:17]=2[CH3:32])[C:10]2[CH:34]=[CH:35][C:36]([Cl:38])=[CH:37][C:9]1=2)=[O:6].[C:39]([N:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1)(=[O:41])[CH3:40].[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O>[C:39]([N:42]1[CH2:47][CH2:46][N:45]([CH2:2][CH2:3][CH2:4][C:5]([O:7][CH:8]2[CH2:14][CH2:13][CH2:12][N:11]([C:15](=[O:33])[C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:31])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[CH3:30])=[CH:18][C:17]=3[CH3:32])[C:10]3[CH:34]=[CH:35][C:36]([Cl:38])=[CH:37][C:9]2=3)=[O:6])[CH2:44][CH2:43]1)(=[O:41])[CH3:40]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 837951-AcetylpiperazineHCID 667334127-Chloro-1-(2-methyl-4-(2-methylbenzamido)benzoyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl 4-chlorobutyrate

Product 1

HCID 667331607-chloro-1-(2-methyl-4-(2-methylbenzamido)benzoyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl 4-(4-acetylpiperazin-1-yl)butyrateYield 51.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

7-Chloro-1-(2-methyl-4-(2-methylbenzamido)benzoyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl 4-chlorobutyrate (0.5 g) was dissolved in acetonitrile (10 ml). 1-Acetylpiperazine (0.35 g), sodium iodide (0.41 g), and sodium carbonate (0.19 g) were added to the solution, and the mixture was heated under reflux for 19 hours. The reactant was poured into water, and the mixture was extracted with ethyl acetate, washed with water, dried over sodium carbonate. After filtration and concentration under reduced pressure, the residue was purified by silica gel column chromatography (dichloromethane:methanol=100:1→100:10) to obtain 0.3 g of 7-chloro-1-(2-methyl-4-(2-methylbenzamido)benzoyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl 4-(4-acetylpiperazin-1-yl)butyrate as colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 19 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over sodium carbonate
  6. filtrationAfter filtration and concentration under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (dichloromethane:methanol=100:1→100:10)

Sources & evidence

ORD record
ord-1a98d37e07814bdab95b393777556c0c
Source dataset
uspto-grants-2014_07
Patent number
US08785386B2

Reaction notes

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