6,11-Dihydro-5H-dibenz[b,e]azepine → HCID 54506243, compound

HRID 362344Notes

Reaction equation

HRID 362344 reaction equation
[CH:1]1[C:11]2[CH2:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH2:7][NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=1[N+:26]([O-:28])=[O:27])[C:20](Cl)=[O:21].C(N(C(C)C)CC)(C)C>ClCCl>[N+:26]([C:25]1[CH:24]=[CH:23][C:19]([C:20]([N:6]2[CH2:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH2:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=3)=[O:21])=[CH:18][C:17]=1[CH3:16])([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 679746,11-Dihydro-5H-dibenz[b,e]azepineHCID 81531DiisopropylethylamineHCID 30157953-Methyl-4-nitrobenzoyl chloride

Product 1

HCID 54506243HCID 54506243, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.17 g of 6,11-dihydro-5H-dibenz[b,e]azepine, 1.20 g of 3-methyl-4-nitrobenzoyl chloride, 0.80 ml of diisopropylethylamine in 25 ml of dichloromethane is stirred 18 hours at room temperature. The mixture is washed with water and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate. The filtrate is concentrated and diluted while hot with hexane to give 1.40 g of crystals. Recrystallization from dichloromethane-hexane gives 1.26 g of crystals, m.p. 179°-180° C.

Workup

  1. washThe mixture is washed with water
  2. dry with materialdried (Na2SO4)
  3. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  4. concentrationThe filtrate is concentrated
  5. additiondiluted while hot with hexane

Sources & evidence

ORD record
ord-7a1f347c702d486da7e291344be4602b
Source dataset
uspto-grants-1999_02
Patent number
US05869483

Reaction notes

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