Room temperature ionic liquid promoted synthesis of 1,5-benzodiazepine derivatives under ambient conditions

Tetrahedron Letters

Volumn 44, Issue 9, 2003, Pages 1835-1838

  Jarikote, D V ^a   Siddiqui, S A ^a   Rajagopal, R ^a   Daniel, Thomas ^a   Lahoti, R J ^a   Srinivasan, K V ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Benzodiazepines; Green solvent; Ionic liquid; o phenylenediamines

Indexed keywords

BENZODIAZEPINE DERIVATIVE; IMIDAZOLE DERIVATIVE; KETONE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; COLUMN CHROMATOGRAPHY; DRUG SYNTHESIS; ENVIRONMENTAL TEMPERATURE; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE;

EID: 0037463420     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00096-0     Document Type: Article

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28. 19 A solution of OPD/substituted OPD 1 (4.62 mmol) and the ketone 2 (9.72 mmol) in [bbim]Br (4.62 mmol) was stirred at 28°C for 50 min. The completion of reaction was followed by TLC using 30% EtOAc in petroleum ether as eluent. After completion, the reaction mixture was diluted with water (25 ml) and extracted with EtOAc (2×15 ml). The combined organic layer was separated, dried over anhydrous sodium sulphate and the solvent evaporated under reduced pressure to afford the 1,5-benzodiazepines. The products, thus isolated, were pure (single spot on TLC). They were subjected to further purification by chromatography through a column of silica-gel using 20% EtOAc in petroleum ether as eluent and fully characterized. The aqueous layer consisting of the I.L. was subjected to distillation (80°C at 10 mmHg) for 2 h to remove water, leaving behind the I.L. [bbim] Br (recovery 98%), which could be recycled.
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