Ammonia → HCID 68523105, compound

Participants

Reaction Steps

A mixture of 3-(3,4-dichloro-phenyl)-9-methyl-3,9-diaza-bicyclo[3.3.1]nonane (0.50 g, 1.75 mmol), 2,2,2-trichloroethylchloroformate (1.11 g, 5.26 mmol) and toluene (30 ml) was stirred at reflux for 15 h. Water (30 ml) was added and the phases were separated. The organic phase was evaporated. Acetic acid (10 ml) and water (10 ml) and zinc powder (0.57 g, 8.8 mmol) was added. The mixture was stirred for 15 h. Aqueous sodium hydroxide (20 ml, 1 M) was added followed by extraction with dichloromethane (3×10 ml). The crude product was purified by silica get column chromatography using a solvent mixture of dichloromethane, methanol and aqueous ammonia (9:1:1%). Yield 150 mg (32%). The corresponding salt was obtained by addition a mixture of hydrogen chloride solved in diethylether (1 ml, 2 M). Mp 295.4° C. LC-ESI-HRMS of [M+H]+ shows 271.0769 Da. Calc. 271.076879 Da, dev. 0.1 ppm.

Provenance & Evidence