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

HRID 1450186Notes

Reaction equation

HRID 1450186 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 (K2CO3) and concentrated. Purification of the product was conducted on silica gel using ethyl acetate:hexane (5:1→4:1) as the eluant to give the title compound.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. extractionThe resulting mixture was extracted with dichloromethane
  3. dry with materialthe combined organic phases were then dried (K2CO3)
  4. concentrationconcentrated
  5. customPurification of the product

Sources & evidence

ORD record
ord-e2c16a857f2e4b02a37fd904c63a0bdd
Source dataset
uspto-grants-1997_02
Patent number
US05602121

Reaction notes

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