Triethylamine → N-[4-(6,7-Dihydro-dibenzo[b,d]azepine-5-carbonyl)-phenyl]-2-methyl-benzamide

HRID 1288979Notes

Reaction equation

HRID 1288979 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]2[CH2:14][CH2:13][C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[C:10]3[CH:19]=[CH:20][CH:21]=[CH:22][C:9]2=3)=[O:7])=[CH:4][CH:3]=1.C(N([CH2:30][CH3:31])CC)C>ClCCl.C(OCC)(=O)C>[CH:19]1[C:10]2[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13][CH2:14][N:8]([C:6]([C:5]3[CH:23]=[CH:24][C:2]([NH:1][C:6](=[O:7])[C:5]4[CH:4]=[CH:3][CH:2]=[CH:24][C:30]=4[CH3:31])=[CH:3][CH:4]=3)=[O:7])[C:9]=2[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 538444955-(4-Aminobenzoyl)-6,7-dihydro-5H-dibenz[b,d]azepine

Product 1

HCID 44212554N-[4-(6,7-Dihydro-dibenzo[b,d]azepine-5-carbonyl)-phenyl]-2-methyl-benzamideYield 130.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.10 g of 5-(4-aminobenzoyl)-6,7-dihydro-5H-dibenz[b,d]azepine, 0.10 g of triethylamine in 1 ml of dichloromethane is stirred at room temperature for 6 hours. The mixture is diluted with 6 ml of ethyl acetate and the solution washed with 1N HCl, 1N KaOH, brine and dried (Na2SO4). The solvent is removed and the solid purified by chromatography on thick layer silica gel plates with the solvent ethyl acetate-hexane (1:1) to give 90 mg of a pale yellow solid.

Workup

  1. washthe solution washed with 1N HCl, 1N KaOH, brine
  2. dry with materialdried (Na2SO4)
  3. customThe solvent is removed
  4. customthe solid purified by chromatography on thick layer silica gel plates with the solvent ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-20dedf39078b4720966599fd4a82b883
Source dataset
uspto-grants-1998_05
Patent number
US05747487

Reaction notes

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