4-Nitrobenzoyl chloride → 5-dimethylamino-1-(4-nitrobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine

HRID 1291544Notes

Reaction equation

HRID 1291544 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][N:8]([CH3:20])[CH:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[NH:13][CH2:12][CH2:11][CH2:10]1.[N+:21]([C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1)([O-:23])=[O:22]>CC(C)=O.O>[CH3:7][N:8]([CH3:20])[CH:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]([C:28](=[O:29])[C:27]2[CH:26]=[CH:25][C:24]([N+:21]([O-:23])=[O:22])=[CH:32][CH:31]=2)[CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 3

HCID 85024-Nitrobenzoyl chlorideHCID 11430Potassium CarbonateHCID 107977675-dimethylamino-2,3,4,5-tetrahydro-1H-benzoazepine

Product 1

HCID 107358285-dimethylamino-1-(4-nitrobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepineYield 97.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

38.8 g of potassium carbonate was added to a solution of 50 g of 5-dimethylamino-2,3,4,5-tetrahydro -1H-benzoazepine dissolved in 400 ml of acetone and 200 ml of water. To the solution was added 40 g of p-nitrobenzoyl chloride with ice-cooling and stirring. The resulting mixture was stirred overnight at room temperature. The reaction mixture was mixed with an appropriate amount of water. The resulting crystals were collected by filtration and dried to obtain 71 g of 5-dimethylamino-1-(4-nitro-benzoyl)-2,3,4,5-tetrahydro -1H-benzoazepine.

Workup

  1. temperaturecooling
  2. stirringThe resulting mixture was stirred overnight at room temperature
  3. filtrationThe resulting crystals were collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-a18277587df546928cedbae00c0bedd6
Source dataset
uspto-grants-1998_05
Patent number
US05753644

Reaction notes

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