1-((1-Methyl-4-piperidinyl)methyl)piperazine → Ammonia

Participants

Reaction Conditions

Reaction Steps

Ethyl 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,3,4-oxadiazole-2-carboxylate (1.0 g, 2.6 mmol) and 1-[(1-methylpiperidin-4-yl)methyl]piperazine (1.03 g, 5.2 mmol) were dissolved in DCE (5 mL) and stirred at 0° C. prior to degassing with N2. Trimethylaluminium (2M in toluene, 2.6 mL) was added dropwise to this solution. Upon complete addition, the reaction was stirred for 1 h at 80° C. The reaction was cooled, diluted with DCM (30 mL) and washed with saturated aqueous NaHCO3 (30 mL). The aqueous layer was extracted with DCM (2×30 mL) and the combined organic extracts dried over MgSO4 and concentrated in vacuo. The resulting brown oil was purified by FCC, eluting with 98:2 DCM:7N NH3 in MeOH to afford the title compound.

Provenance & Evidence