Benzaldehyde → 2-[4-(2-Benzylaminoethyl)phenoxy]nicotinamide

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Reaction Steps

Take up 2-[4-(2-aminoethyl)phenoxy]nicotinamide (0.0555 g, 0.216 mmol) in methanol (2.1 mL). Add benzaldehyde (0.022 mL, 0.216 mmol) and 3 Å molecular sieves. Stir at room temperature overnight. Add NaBH4 (0.0082 g, 0.216 mmol) and stir for 6 hours before loading directly onto an SCX column. Wash the column with methanol then elute with 2.0 M NH3 in methanol. Purify by flash chromatography, eluting with 4% (2.0 M NH3 in methane) in dichloromethane to give the title compound (0.831 g, 79%): TOF MS ES+ 348.2 (M+H)+, HRMS calcd for C21H22N3O2 348.1712 (M+H)+, found 348.1721, time 0.35 min; TLC [silica gel 60 F254, 5% (2.0 M NH3 in methanol) in dichloromethane] Rf=0.20.

Provenance & Evidence