Sodium hydride → HCID 44464434, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-hydroxy-5-methyl-1-(7-methoxynaphthalen-2-yl)-1H-pyrazol (1.51 g, 5.96 mmol) in dimethylformamide (40 ml), cooled down to 0° C., a dispersion in mineral oil at 60% of NaH (0.36 g, 8.94 mmol) was added, the cooling bath was removed, and was left to stirring until it recovered the room temperature (1.5 hrs). Subsequently, 2-chloroethylmorpholine (1.02 g, 6.85 mmol) dissolved in DMF (10 ml) was added dropwise, and the resulting mixture was heated at 60° C. during 20 hrs. Water-ice was added and it was evaporated to dryness in a rotavapor. The resulting slurry was divided between water and ethyl ether. The aqueous phase was newly extracted with a solvent, and the collection of organic phases was washed with water, dried over sodium sulfate, filtered, and evaporated yielding 2.19 g of a crude product, which was purified by crystallization of its chlorhydrate (prepared by dissolving in HCl-saturated dioxane) in isopropyl alcohol-ethyl ether. 1.78 g (74%) of the 4-{2-[1-(7-methoxynaphthalen-2-yl)-5-methyl-1H-pyrazol-3-yloxy]ethyl}morpholine chlorhydrate were obtained as a solid with a m.p.=143-147° C.

Provenance & Evidence