Formaldehyde → N-[2-(3,4-Dimethoxyphenyl)ethyl]-4-[5-methoxy-2-(phenylethynyl)phenyl]-N-methylbutan-2-amine

Participants

Reaction Steps

A mixture of of N-[2-(3,4-dimethoxyphenyl)ethyl]-5-methoxy-α-methyl-2-(phenylethynyl)benzenepropanamine (0.3 g, 0.68 mmole), the free base of the product of Example 1e, and 37% aqueous formaldehyde (0.5 mL) were combined in absolute methanol (5 mL). With stirring, sodium borohydride (0.05 g, 1.3 mmole) was added, and the resulting reaction mixture stirred overnight. The mixture was concentrated in vacuo, the resulting residue dissolved in 5 mL of EtOAc, 5 mL of 1N sodium hydroxide was added and the resulting layers separated. The aqueous layer was extracted with EtOAc and washed with water, brine and dried over anhydrous sodium sulfate. After filtering, the filtrate was concentrated in vacuo to give 0.3 g of the title product as a golden oil. The title product is the antihypertensive pharmaceutical prepared in Example 32 of European Pat. No. 146,271.

Provenance & Evidence