Ammonium Hydroxide → HCID 12051397, compound

Participants

Reaction Conditions

Reaction Steps

5-(1-azabicyclo[2.2.2]oct-2-yl)-3-(bromo)pyridine (120 mg), was mixed with aqueous ammonium hydroxide (20 mL, 28%) in a sealed tube, copper sulfate (200 mg) was added, and the reaction mixture was heated at 180° C. for 14 hours. The reaction mixture was allowed to cool to ambient temperature and then extracted with chloroform (4×20 mL). The combined organic extracts were dried over anhydrous potassium carbonate, filtered, and the solvent removed on a rotary evaporator to afford a dark syrup. This crude product was subjected to column chromatography over silica gel using chloroform:methanol:triethylamine (9:1:1) to yield an initial fraction of 5-(1-azabicyclo[2.2.2]oct-2-yl)-3-(amino)pyridine, which after removal of solvent afforded a light brown solid (20 mg) homogeneous on TLC (silica, chloroform:methanol 95:5). An impure fraction was also obtained, which afforded a brown solid (40 mg), found to be mostly the desired compound with minor impurities on TLC analysis (total yield ˜65%).

Provenance & Evidence