Diethyl Ether → HCID 10567950, compound

Participants

Reaction Steps

To a flame-dried flask containing a mixture of methyllithium (1.5M in ether as complexed with lithium bromide, 5.2 ml) in anhydrous ether (5.2 ml) at -78° under nitrogen is added a solution of 1-benzyl-4-(N-methyl-N-(3-cyano-2-pyridyl)amino)piperidine (XXXIII, EXAMPLE 42, 1.2 g) in anhydrous ether (5.3 ml) over 5 min. The resulting mixture is allowed to warm up to 0° over approximately 2.25 hrs and is quenched with sulfuric acid (2N, 3.9 ml) and stirred at 20°-25° for 2 hrs. The biphasic mixture is then adjusted to pH 10-11 with aqueous sodium hydroxide (5%), diluted with ether (10 ml) and water (10 ml) and the phases are separated. The aqueous phase is extracted with additional ether (30 ml), and the combined organic phases are washed with saline (10 ml), dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and chromatographed (silica gel, 70-230 mesh, 50 g; ethyl acetate/hexane (50/50)) to give the title compound, mp=93°-94°.

Provenance & Evidence