Benzaldehyde → 2-[3-(1-Benzylpiperidin-4-ylidene)prop-1-ynyl]-6-methylpyridine

Participants

Reaction Steps

A mixture of the compound of Example 3 (0.22 g, 1.04 mmol), benzaldehyde (0.13 mL, 1.25 mmol), sodium triacetoxyborohydride (0.33 g, 1.56 mmol) and 15 mL of CH2Cl2 was stirred overnight at r.t. Afterwards, it was diluted with water, the organic layer was separated, washed with brine (2×15 mL), dried (Na2SO4) and evaporated to dryness in vacuo the give a crude, which was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with a gradient Petroleum Ether-EtOAc from 85:15 to 0:100 affording the title compound, which was further purified by preparative RP LC-MS chromatography, using MS-C18 XTerra column 30×50 mm eluting with ammonium bicarbonate 20 mM pH 8 buffer-acetonitrile gradient (0.12 g).

Provenance & Evidence