N-Methylbenzylamine → 4-(N-benzyl-N-methylaminoacetyl)pyridine

Participants

Reaction Steps

To a solution of N-benzyl-N-methylamine (3.7 cm3) in dry dichloromethane (40 cm3), cooled to 0° C. was added with stirring, 4-bromoacetylpyridine hydrobromide (4.0 g). The reaction was allowed to warm to room temperature, then stirred for a further 18 hr. The solvent was stripped at reduced pressure, and the residue partitioned between ethyl acetate and dilute aqueous Na2CO3. The organic phase was separated, dried (Na2SO4), evaporated, and the residue subjected to chromatography on silica gel, eluent 5% methanol in dichloromethane, to afford 4-(N-benzyl-N-methylaminoacetyl)pyridine, 1.49 g, 43%, as a yellow gum.

Provenance & Evidence