Ammonium Hydroxide → HCID 15428881, compound

HRID 1940449Notes

Reaction equation

HRID 1940449 reaction equation
[C:1]([C:3]1[CH:18]=[CH:17][C:6]2[S:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[C:10](=O)[CH2:11][C:5]=2[CH:4]=1)#[N:2].[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.[NH4+].[OH-]>C1(C)C=CC=CC=1.Cl[Ti](Cl)(Cl)Cl>[C:1]([C:3]1[CH:18]=[CH:17][C:6]2[S:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[C:10]([N:23]3[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]3)=[CH:11][C:5]=2[CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 531671-MethylpiperazineHCID 15428880HCID 15428880, compound

Product 1

HCID 15428881HCID 15428881, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 2-cyano-10-oxo-dibenzo[b,f]thiepine (0.10 g, 0.40 mmol) in dry toluene (10.00 mL), was added methyl piperazine (0.21 mL, 1.80 mol) followed by the dropwise addition of TiCl4 (1M in toluene, 1.60 mL, 1.6 mol) via syringe. The mixture was stirred at room temperature for 30 min then refluxed for 5 h. The reaction mixture was cooled, dumped into conc NH4OH and extracted with CHCl3. The combined organic phases were dried (MgSO4) and concentrated in vacuo to dryness. The crude material was chromatographed (20%MeOH/EtOAc) to give 2-cyano-10-(4-methyl-piperazinyl)-dibenzo [b,f]thiepine; yield 0.05 g, (5%).

Workup

  1. temperaturethen refluxed for 5 h
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with CHCl3
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. concentrationconcentrated in vacuo to dryness
  6. customThe crude material was chromatographed (20%MeOH/EtOAc)

Sources & evidence

ORD record
ord-4db2ad8e9fce4ba79a4c5d984079c452
Source dataset
uspto-grants-1997_12
Patent number
US05700445

Reaction notes

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