10,11-Dihydro-5h-dibenzo[b,e][1,4]diazepine → (4-Cyclohexyl-phenyl)-(5,11-dihydro-10H-dibenzo[b,e][1,4]diazepin-10-yl)methanone

HRID 1826671Notes

Reaction equation

HRID 1826671 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.[CH:25]1([C:31]2[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>ClCCl>[CH:25]1([C:31]2[CH:32]=[CH:33][C:34]([C:35]([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:36])=[CH:38][CH:39]=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

5

Reactant 3

HCID 3604610,11-Dihydro-5h-dibenzo[b,e][1,4]diazepineHCID 81531DiisopropylethylamineHCID 218908474-Cyclohexylbenzoyl chloride

Product 1

HCID 10110456(4-Cyclohexyl-phenyl)-(5,11-dihydro-10H-dibenzo[b,e][1,4]diazepin-10-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5,11-Dihydro-10H-dibenzo[b,e][1,4]diazepine (1.96 g) in dichloromethane (50 mL) containing N,N-diisopropylethyl amine (1.3 g) was reacted with the crude 4-cyclohexylbenzoyl chloride prepared as described above (2.22 g). The reaction mixture was kept at room temperature overnight, then washed with water and saturated aqueous sodium bicarbonate. The solution was dried over anhydrous sodium sulfate and filtered through a short column of Magnesol® which was eluted with several additional volumes of dichloromethane. The total effluent was refluxed with the gradual addition of hexane until crystallization was noted. Cooling and filtration afforded the title compound as colorless crystals (1.28 g), m.p. 175–176° C.

Workup

  1. customprepared
  2. washwashed with water and saturated aqueous sodium bicarbonate
  3. dry with materialThe solution was dried over anhydrous sodium sulfate
  4. filtrationfiltered through a short column of Magnesol® which
  5. washwas eluted with several additional volumes of dichloromethane
  6. temperatureThe total effluent was refluxed with the gradual addition of hexane until crystallization
  7. temperatureCooling
  8. filtrationfiltration

Sources & evidence

ORD record
ord-c2c2a34b0d19410fabfa3fed717165d7
Source dataset
uspto-grants-2006_05
Patent number
US07053083B2

Reaction notes

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