3-Pyridinecarboxaldehyde → N-(3-(2-Methoxyphenoxy)phenyl) pyrid-3-ylmethylamine

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(2-methoxyphenoxy)aniline (269 mg, 1.25 mmol) and pyridine-3-carboxaldehyde (107 mg, 1.00 mmol) was refluxed in methanol (2.5 mL) for 2 h, then cooled on an ice bath to 5° C. Sodium borohydride (95 mg, 2.5 mmol) was added and the mixture was warmed to room temperature, stirred for 2 h, concentrated in vacuo, and taken up in dichloromethane. The resultant suspension was filtered, the filtrate concentrated in vacuo, and the residue chromatographed on silica gel (eluted with 2% methanol/dichloromethane) to give N-(3-(2-methoxyphenoxy)phenyl)pyrid-3-ylmethylamine.

Provenance & Evidence