Hydrochloric Acid → 4-{[3-(3,8-Diazabicyclo[3.2.1]oct-8-yl)propyl]amino}benzonitrile

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Reaction Steps

To a cold solution of 4-{[3-(3-benzyl-3,8-diazabicyclo[3.2.1]oct-8-yl)propyl]amino}benzonitrile (6.26 g, 17.4 mmol; from step (c) above) in acetonitrile (100 mL) was added 12 M HCl (5.8 mL). The reaction mixture was stirred for 15 minutes, concentrated in vacuo and dried under high vacuum overnight. The resulting hydrochloride salt was added to a suspension of 10% Pd/C (800 mg) in methanol (250 mL). The reaction was then stirred under hydrogen (1 atmosphere of pressure) for 50 min. The mixture was filtered through Celite® and the filtrate was concentrated in vacuo. The resulting residue was partitioned with saturated NaHCO3 (100 mL) and CH2Cl2 (200 mL). The organic layer was dried (Na2SO4), filtered and concentrated ill vacuo to give the crude product. Flash chromatography on silica gel eluting with a gradient of CH2Cl2:CMA (4:1 to 2:1) gave 2.02 g (43%) of the title compound.

Provenance & Evidence