N-Methylbenzeneethanamine → 9-(Methyl-phenethyl-amino)-nonanoic acid methyl ester

Participants

Reaction Steps

To a solution of 9-oxononanoic acid methyl ester (J. Org. Chem. 2007, 72, 9471; 303 mg, 1.63 mmol) and N-methyl-2-phenylethylamine (220 mg, 1.63 mmol) in methanol (10 mL) was added concentrated sulfuric acid (5 drops) at room temperature, then after 40 h the solution was heated at reflux for 2 h. After cooling sodium borohydride (123 mg, 3.25 mmol) was added, then after 1 h the reaction mixture was partitioned between water and dichloromethane. The organic layer was dried over sodium sulfate, filtered, and evaporated to afford 9-(methyl-phenethyl-amino)-nonanoic acid methyl ester as a light yellow liquid.

Provenance & Evidence