1,5-diazabicyclo[3.2.2]nonane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound of Example 2 (1.70 g, 12.1 mmol) was added portionwise at room temperature to a stirred solution of AIH3 (60 mL of a 1.0M solution, 60 mmol). The solution became warm. Stirring was continued for a further 20 minutes and the reaction mixture was poured into cold (5° C.) 30% aqueous KOH solution (100 mL) and the aqueous mixture was extracted with CHCl3 (200 mL). The organic extract was dried (Na2SO4) and evaporated to give the title compound in quantitative yield: mp 250° C. (dec) (EtOH); 1H-NMR (CDCl3) δ 3.02-3.25 (m, 1H), 2.66-3.02 (complex m, 3H), 2.59 (m, 1H), 2.43 (m, 1H), 2.25-2.40 (m, 1H), 1.87 (m, 1H), 1.04-1.77 (complex m, 6H); Anal (calcd for C17H16Cl2N2 ·0.33H2O): C 40.99, H 8.19, N 13.66. Found C 41.00, H 8.31, N 13.68. The solution became warm the aqueous mixture was extracted with CHCl3 (200 mL) The organic extract was dried (Na2SO4) evaporated