Benzaldehyde → 6-(1-benzylpiperidin-3-yloxy)-2H-isoquinolin-1-one

Participants

Reaction Conditions

Reaction Steps

Sodium triacetoxyborohydride (100 mg, 3.9 mol eq) was added to a solution of 1-chloro-6-(piperidin-3-yloxy)isoquinoline (40mg), acetic acid (1 drops) and benzaldehyde (40 μl) in N, N-dimethylformamide (0.5 ml) and shaken for 17 hours. The reactions were quenched with water (0.5 ml) and shaken for 1 h then loaded onto a pre-acidified SCX column using methanol and eluted with 2M ammonia in methanol. The product was concentrated in vacuo to give a residue which was treated with 5M aqueous hydrochloric acid and heated in the microwave at 180° C. for 60 minutes. The mixture was concentrated in vacuo to give a residue which was purified by prep-HPLC to give 6-(1-benzylpiperidin-3-yloxy)-2H-isoquinolin-1-one, El-MS: m/z=335.7 [M+H]+.

Provenance & Evidence