Piperazine → 11-(Piperazin-1-yl)dibenzo(b,f)(1,4)oxazepine

HRID 355669Notes

Reaction equation

HRID 355669 reaction equation
[CH:1]1[C:6]2[C:7](=O)[NH:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.[OH-].[NH4+]>C1(C)C=CC=CC=1.Cl[Ti](Cl)(Cl)Cl>[N:17]1([C:7]2[C:6]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[O:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[N:8]=2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1

Participants

6

Reactant 3

HCID 4837PiperazineHCID 14923Ammonium HydroxideHCID 72374O-(o-Aminophenoxy)benzoic acid lactam

Product 1

HCID 706187411-(Piperazin-1-yl)dibenzo(b,f)(1,4)oxazepine

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent

Procedure

To a stirred solution of 10,11-dihydro-dibenz[b,f][1,4]oxazepin-11-one in dry toluene at room temperature was added piperazine (Aldrich) followed by the dropwise addition of TiCl4. The reaction mixture was refluxed for 2 hours, cooled to room temperature and then poured into an ammonium hydroxide solution. The resulting mixture was extracted with dichloromethane, and the combined organic phases were then dried (K2 CO3) and concentrated. Purification of the product was conducted on silica gel using ethyl acetate:hexane (5:1→4:1) as the eluant to give 11-(1-piperazinyl)dibenz[b,f][1,4]oxazepine.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. extractionThe resulting mixture was extracted with dichloromethane
  3. customthe combined organic phases were then dried (K2 CO3)
  4. concentrationconcentrated
  5. customPurification of the product

Sources & evidence

ORD record
ord-3ffba3ab609a478e960d7a9d4a798ae0
Source dataset
uspto-grants-1998_11
Patent number
US05834459

Reaction notes

Loading…