Dimethylamine → tert-Butyl 4-[1-dimethylamino-3-(6-methylpyridin-2-yl)prop-2-ynyl]piperidine-1-carboxylate

Participants

Reaction Steps

A mixture of 2-ethynyl-6-methyl-pyridine (0.08 g, 0.7 mmol), 1-Boc-4-piperidinecarboxaldehyde (0.1 g, 0.47 mmol), CuI (0.001 g, 0.11 mmol) and 33% w/w aqueous dimethylamine (0.077 mL, 0.56 mmol) in water (3 mL) was sonicated for 2 h in a laboratory ultrasonic bath. Afterwards, it was extracted with EtOAc and the combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to give a crude, which was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with EtOAc—Petroleum Ether 1:1 affording the title product (0.11 g).

Provenance & Evidence