10,11-Dihydro-5h-dibenzo[b,e][1,4]diazepine → HCID 22099538, compound

HRID 1457708Notes

Reaction equation

HRID 1457708 reaction equation
[CH:1]1[C:11]2[CH2:10][NH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)C(C)C)(C)C.[S:25]1[CH:29]=[CH:28][C:27]([C:30]2[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=2)=[CH:26]1>ClCCl>[S:25]1[CH:29]=[CH:28][C:27]([C:30]2[CH:38]=[CH:37][C:33]([C:34]([N:9]3[CH2:10][C:11]4[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=4[NH:6][C:7]4[CH:15]=[CH:14][CH:13]=[CH:12][C:8]3=4)=[O:35])=[CH:32][CH:31]=2)=[CH:26]1

Participants

5

Reactant 3

HCID 3604610,11-Dihydro-5h-dibenzo[b,e][1,4]diazepineHCID 81531DiisopropylethylamineHCID 220996674-(Thiophen-3-yl)benzoyl chloride

Product 1

HCID 22099538HCID 22099538, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a mixture of 2.0 g of 5,11-dihydro-10H-dibenz[b,e][1,4]diazepine and 7 ml of N,N-diisopropylethylamine in 30 ml of dichloromethane is added dropwise a solution of 3.15 g of 4-(3-thienyl)benzoyl chloride in 30 ml of dichloromethane. The mixture is stirred 16 hours at room temperature and diluted with dichloromethane (50 ml). The solution is washed with 30 ml each of H2O, 2N HCl, saturated NaHCO3, water and dried (Na2SO4). The solvent is removed under vacuum and the residue purified by chromatography on silica gel with hexane-ethyl acetate as eluent to give a solid.

Workup

  1. washThe solution is washed with 30 ml each of H2O, 2N HCl, saturated NaHCO3, water
  2. dry with materialdried (Na2SO4)
  3. customThe solvent is removed under vacuum
  4. customthe residue purified by chromatography on silica gel with hexane-ethyl acetate as eluent
  5. customto give a solid

Sources & evidence

ORD record
ord-15e8bf8054584e468d031d18f3f70bde
Source dataset
uspto-grants-1998_12
Patent number
US05849735

Reaction notes

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