Hydrochloric Acid → HCID 178487566, compound

Participants

Reaction Conditions

Reaction Steps

To NaH (60 wt. % dispersion in oil; 0.42 g, 10.5 mmol) suspended in THF (20 mL) was added 1,1-dimethylethyl 4-({[4-(cyanomethyl)-2-(methyloxy)phenyl]oxy}methyl)piperidine-1-carboxylate (1.73 g, 4.81 mmol) and then anhydrous ethyl acetate (0.559 mL, 5.73 mmol). The mixture was stirred at 60° C. for 15 h. The mixture was cooled to room temperature, was acidified with 4 N HCl in dioxane (2 mL, 8 mmol) and was concentrated in vacuo. The residue was partitioned between 1 N hydrochloric acid and ethyl acetate. The organic portion was washed with water, brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford a red oil which was dissolved in ethanol (20 mL) and treated with hydrazine (0.185 mL, 5.84 mmol) at reflux for 1 h. The mixture was concentrated in vacuo and dried in vacuo to afford 1,1-dimethylethyl 4-({[4-(5-amino-3-methyl-1H-pyrazol-4-yl)-2-(methyloxy)phenyl]oxy}methyl)piperidine-1-carboxylate as a red foam (2.00 g, 4.81 mmol, 100% yield). MS (EI) for C22H32N4O4: 417 (MH+), 439 (MNa+).

Provenance & Evidence