Potassium Hydroxide → HCID 10710035, compound

Participants

Reaction Steps

A mixture of 1-benzyl-4-(N-methyl-N-(3-acetyl-2-pyridyl)amino)piperidine (XXXIV, EXAMPLE 43, 260 mg), hydrazine monohydrate (0.78 ml) and powdered potassium hydroxide (0.90 g) in triethylene glycol (16 ml) is stirred at 120° for 2 hrs. The condenser is removed, the mixture is heated up to approximately 185°-190°, the condenser is replaced, and the mixture is stirred at 190° for 3 hrs. After cooling to 20°-25°, the mixture is added to water (50 ml) and extracted with methylene chloride (2×50 ml), and the organic phase is washed with water (20 ml) and saline (20 ml), dried over sodium sulfate, concentrated under reduced pressure and chromatographed (silica gel, 70-230 mesh, 25 g; eluting with a gradient of ethyl acetate/hexane (25/75→50/50)) to give the title compound, NMR (CDCl3, 400 MHz) 8.16, 7.46, 7.31, 7.26, 6.88, 3.50, 3.15, 2.92, 2.73, 2.63, 2.00, 1.82, 1.73 and 1.23δ.

Provenance & Evidence