Ammonium Hydroxide → 11-(2-Benzyl-2,5-diazabicyclo(2.2.1) hept-5-yl)-dibenz[b,f][1,4]oxazepine

HRID 1488472Notes

Reaction equation

HRID 1488472 reaction equation
O=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[NH:3]1.[CH2:17]([N:24]1[CH2:29][C@@H:28]2[CH2:30][C@H:25]1[CH2:26][NH:27]2)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[NH4+].[OH-]>C1(C)C=CC=CC=1.Cl[Ti](Cl)(Cl)Cl>[CH2:17]([N:24]1[CH2:29][CH:28]2[CH2:30][CH:25]1[CH2:26][N:27]2[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[N:3]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 72374O-(o-Aminophenoxy)benzoic acid lactamHCID 14612543(1S,4S)-2-Benzyl-2,5-Diazabicyclo[2.2.1]heptane

Product 1

HCID 2209953111-(2-Benzyl-2,5-diazabicyclo(2.2.1) hept-5-yl)-dibenz[b,f][1,4]oxazepineYield 49.1%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 11-oxo-dibenz[b,f][1,4]oxazepine (Aldrich) (0.149 g, 0.0007 mol) in dry toluene (10 mL), was added (1S,4S)-2-benzyl-2,5-diazabicyclo(2.2.1)heptane (0.54 g, 0.003 mol) and TiCl4 (0.75 mL, 0.0008 mol) via syringe. The mixture was stirred at room temperature for 30 min then refluxed for 5 hrs. The reaction mixture was cooled and dumped into conc. NH4OH and extracted with CHCl3. The combined organic phases were dried (MgSO4) and concentrated in vacuo. The crude material was chromatographed (hexane:EtOAc, 1:1) to give 11-(2-benzyl-2,5-diazabicyclo(2.2.1) hept-5-yl)-dibenz[b,f][1,4]oxazepine (yield 0.131 g, mp 70°-72° C.).

Workup

  1. temperaturethen refluxed for 5 hrs
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with CHCl3
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude material was chromatographed (hexane:EtOAc, 1:1)

Sources & evidence

ORD record
ord-1ed58932397245018fc1e7032e4463b7
Source dataset
uspto-grants-1997_10
Patent number
US05674877

Reaction notes

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