Phosphorus pentachloride → 5-(4-methyl-1-homopiperazinyl)-11H-imidazo[1,2-c][1,3]benzodiazepine

HRID 1462328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1462328
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]([N:16]1[CH2:22][CH2:21][CH2:20][N:19]([CH3:23])[CH2:18][CH2:17]1)=O.P(Cl)(Cl)(Cl)(Cl)Cl>P(Cl)(Cl)(Cl)=O>[CH3:23][N:19]1[CH2:20][CH2:21][CH2:22][N:16]([C:14]2[N:3]3[CH:4]=[CH:5][N:1]=[C:2]3[CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:13]=2)[CH2:17][CH2:18]1

Komponenten

4

Edukt 2

HCID 24819Phosphorus pentachlorideHCID 133449231-[2-(2-Imidazolylmethyl)phenylcarbamoyl]-4-methylhomopiperazine

Produkt 1

HCID 133449135-(4-methyl-1-homopiperazinyl)-11H-imidazo[1,2-c][1,3]benzodiazepine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24813Phosphorus oxychlorideLösungsmittel

Versuchsvorschrift

To a suspension of 2.46 g of 1-[2-(2-imidazolylmethyl)phenylcarbamoyl]-4-methylhomopiperazine in 19.4 ml of phosphorus oxychloride was added at once 1.66 g of phosphorous pentachloride and the mixture was stirred at room temperature for 4 hours. The mixture was evaporated to dryness, the residue was suspended in 45.2 ml of methylene chloride, the suspension was cooled to 0° and 21.4 ml of triethylamine were added dropwise with stirring over a period of 15 minutes. The mixture was allowed to warm up to room temperature, stirred for 1.5 hours and poured into 10% aqueous potassium carbonate. The methylene chloride layer was separated, the aqueous layer was washed with methylene chloride and the combined methylene chloride extracts were dried over MgSO4, decolorized with charcoal and evaporated to dryness. The residue was purified by column chromatography with 50 g of silica gel, using methylene chloride-methanol-conc. ammonium hydroxide (300:50:1) as eluent to give 5-(4-methyl-1-homopiperazinyl)-11H-imidazo[1,2-c][1,3]benzodiazepine as an oil. This free base was dissolved in acetone and treated with maleic acid to give 5-(4-methyl-1-homopiperazinyl)-11H-imidazo[1,2-c][1,3]benzodiazepine monomaleate, m.p. 160°-163°.

Aufarbeitung

  1. customThe mixture was evaporated to dryness
  2. temperaturethe suspension was cooled to 0°
  3. addition21.4 ml of triethylamine were added dropwise
  4. stirringwith stirring over a period of 15 minutes
  5. temperatureto warm up to room temperature
  6. stirringstirred for 1.5 hours
  7. additionpoured into 10% aqueous potassium carbonate
  8. customThe methylene chloride layer was separated
  9. washthe aqueous layer was washed with methylene chloride
  10. dry with materialthe combined methylene chloride extracts were dried over MgSO4
  11. customevaporated to dryness
  12. customThe residue was purified by column chromatography with 50 g of silica gel

Quellen und Nachweise

ORD-Eintrag
ord-b8e83050e57e4d7a9b77f2455d1db687
Quelldatensatz
uspto-grants-1984_07
Patentnummer
US04460508

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