1-Benzyl-4-[N-methyl-N-(3-(1-ethoxycyclopropylamino)-2-pyridinyl)amino]piperidine → 1-Benzyl-4-[N-methyl-N-(3-(cyclopropylamino)-2-pyridinyl)amino]piperidine

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Reaction Steps

A mixture of 1-benzyl-4-[N-methyl-N-(3-(1-ethoxycyclopropylamino)-2-pyridinyl)amino]piperidine (EXAMPLE 123, 178 mg) in dry tetrahydrofuran (4.7 ml) under nitrogen is treated with lithium aluminum hydride (18 mg), and the resulting mixture is stirred at 20°-25° for 1 hr, quenched with saturated aqueous ammonium chloride (5 ml), diluted with water (30 ml) and methylene chloride (20 ml), and filtered through diatomaceous earth. The layers of the filtrate are separated, the aqueous phase is extracted with methylene chloride (2×10 ml), and the combined organic phase is washed with saline (10 ml), dried over sodium sulfate and concentrated under reduced pressure. The crude product is then chromatographed (silica gel 230-400 mesh, 40 g; eluting with a gradient of methanol/methylene chloride (2.5/97.5-5/95)) to give the title compound, NMR (CDCl3) 7.75, 7.31. 7.24, 7.21, 6.92, 4.92, 3.50, 3.04, 2.89, 2.62, 2.35, 1.99, 1.70, 0.75 and 0.51δ.

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