Sodium Hydroxide → 3,N-Dimethyl-2-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-N-phenethyl-butyramide

Participants

Reaction Steps

A mixture of 2-amino-3,N-dimethyl-N-phenethyl-butyramide (1.5 g, 6.48 mmol), 5-nitro-2-phenoxy-pyridine-4-carbaldehyde (1.5 g, 6.1 mmol), dichloromethane (75 mL), and THF (75 mL) was stirred for 5 hrs. Sodium triacetoxyborohydride (3.0 g, 14.25 mmol) was then added and the resulting mixture was stirred 16 hrs. Sodium hydroxide solution ([0.1 N], 100 mL) was added, the organic layer was separated, treated with MgSO4, filtered and the solvent evaporated to yield an oil. The oil was purified by column chromatography (10%-40% ethyl acetate/heptane) to yield a residue.

Provenance & Evidence