3-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine → HCID 178516517, compound

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Reaction Steps

3-[3-(Piperidinomethyl)phenoxy]propylamine (14.84 g) and 2-bromopyrid-4-one (5.20 g) were stirred together at 165°-170° C. for 4 hours. The reaction mixture was cooled to give a dark orange glassy solid which was dissolved in 2N hydrochloric acid to give a solution having a pH of 4.5. This solution was washed thoroughly with diethyl ether (8×) and chloroform (4×) to remove residual 2-bromopyrid-4-one and some by-product. The aqueous phase was taken to pH 9-10 with 2N sodium hydroxide and extracted into chloroform (9×). The chloroform extracts were combined, dried and evaporated under reduced pressure to afford a dark orange oil. This oil was subjected to medium pressure column chromatography on silica gel using gradient elution; ethyl acetate→10% methanol:90% ethyl acetate. The desired fractions were collected, combined and evaporated under reduced pressure to give the title compound (6.0 g) as a yellow-orange oil which was washed with diethyl ether.

Provenance & Evidence