(1-Azabicyclo[2.2.2]oct-3-ylmethyl)amine synthesis

Yield:75936-99-1 32%

Reaction Conditions:

with hydrogenchloride;hydrogen;palladium 10% on activated carbon in methanol;water at 0; for 4.5 h;

Steps:

II.7

Concentrated hydrochloric acid (12 mL) and 10% palladium on carbon (9.6 g) were added to a solution of the nitrile (35.0 mmol) in methanol (720 mL) at 0 ⁰C. The reaction mixture was maintained under an atmosphere of hydrogen gas for 4.5 hours. The catalyst was removed by filtration through Celite and the filtrate was concentrated to afford a yellow solid. This solid was dissolved in methanol and re-precipitated with ethyl ether (400 mL). The solids were collected by filtration and dried to provide the desired product in 32% yield as a yellow solid. ¹H NMR (CD₃OD) δ 3.30 (m, 1 H), 3.14 (m, 4 H), 2.90 (m, 2 H), 2.85 (m, 1 H), 2.2 (m 1 H), 2.0 (m, 1 H), 1.85 (m, 2 H), 1.6 (m, 1 H).

References:

WO2006/69097,2006,A2 Location in patent:Page/Page column 47