Ammonia → HCID 9797430, compound

HRID 1940446Notes

Reaction equation

HRID 1940446 reaction equation
C1(OC)C=CC=CC=1.[CH3:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[Cl:16][C:17]1[C:22]2[NH:23][C:24]3[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=3[NH:26][C:27](=O)[C:21]=2[CH:20]=[CH:19][CH:18]=1.N>C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl.C(O)(C)C>[Cl:16][C:17]1[C:22]2[NH:23][C:24]3[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=3[N:26]=[C:27]([N:13]3[CH2:14][CH2:15][N:10]([CH3:9])[CH2:11][CH2:12]3)[C:21]=2[CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 7519AnisoleHCID 531671-Methylpiperazine2×HCID 15428875HCID 15428875, compound

Product 1

HCID 9797430HCID 9797430, compound

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent3×HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of anisole (0.40 mL, 3.68 mmol) in dry toluene (2.00 mL) was added titanium tetrachloride (0.24 mL, 2.18 mmol) at room temperature under argon. The mixture was then treated with 1-methylpiperazine (1.04 mL, 0.94 g, 9.40 mmol) and 4-chloro-11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepine (0.49 g, 2.00 mmol) (Giani et al, supra) and diluted with toluene (1.00 mL). After more 1-methylpiperazine (0.60 mL, 0.54 g, 5.40 mmol) was added, toluene (8.00 mL) was added and the resulting reaction mixture was heated at reflux for 6 h before it was cooled to 60° C. Isopropanol (0.80 mL), celite (0.40 g) and ammonia (30%, 0.50 mL) were added sequentially and the whole mixture was filtered hot. Upon cooling to room temperature, the filtrate was concentrated in vacuo to dryness. The purification was carried out either by acidic (3M HCl) extraction and basification (30% ammonia) or column chromatography using ethyl acetate/methanol (3/1) as the eluent. The title compound was obtained as a light yellow solid in 0.60 g (91%); m.p. 168°-170° C.; MS (EI) 326 (M+).

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 6 h before it
  4. filtrationthe whole mixture was filtered hot
  5. temperatureUpon cooling to room temperature
  6. concentrationthe filtrate was concentrated in vacuo to dryness
  7. customThe purification
  8. extractionwas carried out either by acidic (3M HCl) extraction and basification (30% ammonia) or column chromatography

Sources & evidence

ORD record
ord-f414425c8746455bbab6e55d8b045dfa
Source dataset
uspto-grants-1997_12
Patent number
US05700445

Reaction notes

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