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 2054141Notes

Reaction equation

HRID 2054141 reaction equation
[CH:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.[CH:22]1[C:32]2[CH2:31][NH:30][C:29]3[CH:33]=[CH:34][CH:35]=[CH:36][C:28]=3[NH:27][C:26]=2[CH:25]=[CH:24][CH:23]=1.C(N(CC)C(C)C)(C)C.C1(C2C=CC(C(Cl)=O)=CC=2)CCCCC1>ClCCl.CN(C)C=O>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:11]([N:30]3[CH2:31][C:32]4[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=4[NH:27][C:28]4[CH:36]=[CH:35][CH:34]=[CH:33][C:29]3=4)=[O:13])=[CH:14][CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

8

Reactant 5

HCID 3604610,11-Dihydro-5h-dibenzo[b,e][1,4]diazepineHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 883374-Cyclohexylbenzoic acidHCID 218908474-Cyclohexylbenzoyl chloride

Product 1

HCID 10110456(4-Cyclohexyl-phenyl)-(5,11-dihydro-10H-dibenzo[b,e][1,4]diazepin-10-yl)methanoneYield 33.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4-cyclohexylbenzoic acid (10.0 g) in dichloromethane (75 mL) was added oxalyl chloride (10.0 g) followed by N,N-dimethylformamide (2 drops). The mixture was stirred at room temperature overnight and then all volatiles were removed in vacuo to provide the crude acid chloride (11.0 g). 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. customall volatiles were removed in vacuo
  2. customto provide the crude acid chloride (11.0 g)
  3. customprepared
  4. waitThe reaction mixture was kept at room temperature overnight
  5. washwashed with water and saturated aqueous sodium bicarbonate
  6. dry with materialThe solution was dried over anhydrous sodium sulfate
  7. filtrationfiltered through a short column of Magnesol® which
  8. washwas eluted with several additional volumes of dichloromethane
  9. temperatureThe total effluent was refluxed with the gradual addition of hexane until crystallization
  10. temperatureCooling
  11. filtrationfiltration

Sources & evidence

ORD record
ord-c38d82f1b5dc45d6ab139b3ef170a9de
Source dataset
uspto-grants-2008_02
Patent number
US07329653B2

Reaction notes

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