Hydroxylamine HCl → HCID 136340683, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of hydroxylammonium chloride (1.04 g) in DMSO (10.0 mL) was stirred at 40° C. After stirred at 40° C. for 1 h, a mixture of 4-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}benzonitrile obtained in Example 16 (1.1 g) and sodium hydrogen carbonate (1.26 g) was added to the mixture. After stirred at 90° C. for 1 h, the reaction mixture was partitioned between ethyl acetate and water and separated. The organic layer was washed with saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was dissolved in THF (30.0 mL), added to a mixture of 1,1′-carbonyl bis-1H-imidazole (0.568 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.522 mL) and the resulting reaction mixture was stirred at room temperature for 3 h. After this time, the reaction mixture was poured into 1 M HCl water solution and extracted with ethyl acetate. The combined organics were washed with saturated sodium chloride, dried (MgSO4), filtered, and concentrated under reduced pressure to provide the title compound (1.01 g, 78%) as a solid.

Provenance & Evidence