Hydroxylamine → HCID 21708613, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of crude (1-azabicyclo[2.2.21octan-3-yl)hydroxyiminoacetonitrile (10 g, max. 29 mmol) (example 1 C) in methanol (50 ml) was added a methanol solution of hydroxylamine (prepared from NH2OH, HCl (4.2 g, 60 mmol) in methanol (60 ml) and sodium (1.38 g, 60 mmol) in methanol (60 ml)). The reaction mixture was stirred at 40° C. for 18 h and evaporated to give the crude amide oxime derivative. The residue was treated with excess of POCl3 at 45° C. for 18 h. Water and sodium hydroxide was added to obtain alkaline pH and the aqueous mixture extracted with chloroform. The combined organic phases were dried and evaporated to give the free base of the title compound as a solid (yield 570 mg). MS: M+ : 194. Crystallization as the fumarate salt from isopropanol gave the title compound (110 mg) (Compound 66), M.p. 60°-75° C.

Provenance & Evidence