Potassium Hydroxide → HCID 71073319, compound

Participants

Reaction Steps

To 1-acetyl-4-piperidone (0.877 mmol, 0.109 ml) in dichloromethane (3 ml) and acetic acid (0.143 ml) under nitrogen atmosphere was added 8-methyl-3-(piperidin-4-yl)imidazo[1,5-a]pyrazine (0.797 mmol, 172 mg) in dichloromethane (4 ml) and methanol (1 ml). After 20 minutes, sodium cyanoborohydride (0.877 mmol, 55.1 mg) was added. After stirring at room temperature for one hour 1-acetyl-4-piperidone (0.877 mmol, 0.109 ml) and acetic acid (0.05 ml) were added. After 1.5 hours water was added to the reaction mixture and saturated aqueous sodium hydrogencarbonate solution were added to the water layer and made basic (pH 10) with potassium hydroxide. This aqueous basic mixture was extracted with dichloromethane/methanol (9/1) and the organic extracts concentrated in vacuo. The residue was purified by column chromatography (silica gel; dichloromethane containing 1% triethylamine with gradient 0 to 10% of methanol) to give 1-(4-(8-methylimidazo[1,5-a]pyrazin-3-yl)-1,4′-bipiperidin-1′-yl)ethanone (174 mg).

Provenance & Evidence