Triethylamine → 10,11-Dihydro-10-(4-(4-butyloxy)benzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

HRID 1940820Notes

Reaction equation

HRID 1940820 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[NH:7][CH2:6][C:5]=12.C(N(CC)CC)C.[CH2:22]([O:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1)[CH2:23][CH2:24][CH3:25].[OH-].[Na+]>C(Cl)Cl>[CH3:25][CH2:24][CH2:23][CH2:22][O:26][C:27]1[CH:28]=[CH:29][C:30]([C:31]([N:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][N:4]3[CH:3]=[CH:2][CH:1]=[C:5]3[CH2:6]2)=[O:32])=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 1185614-Butoxybenzoyl chlorideHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine

Product 1

HCID 1891754210,11-Dihydro-10-(4-(4-butyloxy)benzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepineYield 88.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 92 mg of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 2 ml of methylene chloride is added 100 mg of triethylamine followed by 130 mg of 4-(n-butyloxy)benzoyl chloride. The reaction mixture is stirred at room temperature for 24 hours and then treated with 4 ml of 1N sodium hydroxide. The mixture is extracted with 10 ml of ethyl acetate and the extract washed with 1N sodium hydroxide and 5 ml of brine. The organic layer is dried over anhydrous sodium sulfate and filtered through hydrous magnesium silicate. The filtrate is concentrate in vacuo to a residue which is stirred with ether-hexanes to give 160 mg of the desired product as a white solid:mass spectrum(CI), 361 (MH+).

Workup

  1. extractionThe mixture is extracted with 10 ml of ethyl acetate
  2. washthe extract washed with 1N sodium hydroxide and 5 ml of brine
  3. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  4. filtrationfiltered through hydrous magnesium silicate
  5. concentrationThe filtrate is concentrate in vacuo to a residue which
  6. stirringis stirred with ether-hexanes

Sources & evidence

ORD record
ord-d99aae988d1a4412b7aa2f712e3cdbfb
Source dataset
uspto-grants-1997_12
Patent number
US05700796

Reaction notes

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