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

HRID 5579Notes

Reaction equation

HRID 5579 reaction equation
[CH3:1][N:2]([CH3:14])[CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][CH2:6][CH2:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].[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>[CH3:1][N:2]([CH3:14])[CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:28](=[O:29])[C:27]2[CH:26]=[CH:25][C:24]([N+:21]([O-:23])=[O:22])=[CH:32][CH:31]=2)[CH2:6][CH2:5][CH2:4]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

To a solution of 5-dimethylamino-2,3,4,5-tetrahydro-1H-benzazepine (50 g) in a mixture of acetone (400 ml) and water (200 ml) is added potassium carbonate (38.8 g), and thereto is added p-nitrobenzoyl chloride (40 g) with stirring under ice-cooling, and the mixture is stirred at room temperature overnight. To the reaction mixture is added an appropriate amount of water, and the precipitated crystals are collected by filtration and dried to give 5-dimethylamino-1-(4-nitrobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (71 g) as pale yellow powder, mp. 139°-142° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at room temperature overnight
  3. filtrationthe precipitated crystals are collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-e5cdc5322a3f49ad962f9c48c672d656
Source dataset
uspto-grants-1993_09
Patent number
US05244898

Reaction notes

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