5167-08-8

To a slowly stirring suspension of 11.6 g of 13 (0.0523 mol) in 8.7 mL of H2O was added a solution of 8.7 g (0.378 mol) of NaOH in 8.7 mL of H2O, which effected almost complete solution. The resulting solution was extracted three times with CHCl3; the combined extracts were dried with Na2SO4, filtered, and evaporated to give 5.68 g of yellow oil. This was treated with excess concentrated HCl and evaporated to dryness. The semisolid was triturated in acetone and EtOH, quickly filtered, and dried under N2 to yield 6.75 g (70%) dihydrochloride salt, mp 340 ℃ dec (lit.16 mp 348 ℃  dec).^[1]

[1] PRISCILLA A. STURM. Antifilarial agents. 3-Aminopyrrolidine and 1,4-diazabicyclo[3.2.1]octane derivatives as analogs of diethylcarbamazine[J]. Journal of Medicinal Chemistry, 1977, 20 10: 1333-1337. DOI:10.1021/jm00220a021.