Ammonium Hydroxide → HCID 18944941, compound

HRID 399731Notes

Reaction equation

HRID 399731 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.[CH3:17][CH:18]1[CH2:23][NH:22][CH2:21][CH:20]([CH3:24])[NH:19]1.[OH-].[NH4+]>C1(C)C=CC=CC=1.Cl[Ti](Cl)(Cl)Cl>[CH3:17][CH:18]1[NH:19][CH:20]([CH3:24])[CH2:21][N:22]([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)[CH2:23]1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 660562,6-DimethylpiperazineHCID 72374O-(o-Aminophenoxy)benzoic acid lactam

Product 1

HCID 18944941HCID 18944941, compoundYield 60.4%

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 (0.4 g; 1.9 mmol; Aldrich) in dry toluene (20 mL) at room temperature was added 2,6-dimethyl piperazine (0.99 g; 8.7 mmol; Aldrich) followed by the dropwise addition of TiCl4 (1M in toluene, 2.27 mL; 2.27 mmol). The reaction mixture was refluxed for 2 hours, cooled to room temperature and then poured into an ammonium hydroxide solution (30%, 50 mL). The resulting mixture was extracted with dichloromethane (4×75 mL), and the combined organic phases were then dried (K2CO3) and concentrated. Purification of the product was conducted on silica gel using CHCl3 :MeOH (94:6) eluant to give 0.353 g (60%) of 11-(3,5-dimethyl-1-piperazinyl)-dibenz[b,f][1,4]oxazepine as a pale yellow solid; m.p. 112°-114° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. extractionThe resulting mixture was extracted with dichloromethane (4×75 mL)
  3. dry with materialthe combined organic phases were then dried (K2CO3)
  4. concentrationconcentrated
  5. customPurification of the product

Sources & evidence

ORD record
ord-775a3fd0caea4ceba23b815c6b802f9f
Source dataset
uspto-grants-1998_10
Patent number
US05824676

Reaction notes

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