Triethylamine → Methyl 6-[2-(3,5-dimethylphenoxy)acetylamino]hexanoate

Participants

Reaction Steps

In a 5L 3-necked flask equipped with a mechanical stirrer and a dropping funnel was placed 1,1′-carbonyldiimidazole (94.4 g, 0.583 mol) in dichloromethane (1 L). A solution of 3,5-dimethylphenoxyacetic acid (Intermediate A77, 95.4 g, 0.53 mol) in dichloromethane (1250 mL) was added over a period of 60 min under argon. Triethylamine (107.1 g, 1.06 mol) was added followed by addition of a suspension of methyl 6-aminohexanoate hydrochloride (101.1 g, 0.555 mol) in dichloromethane (250 mL) in five portions. After 1 hr the reaction mixture was washed with 3 M HCl (1×1L), 2 M ammonium hydroxide (1×1L), and water (1×1L). The organic phase was then filtered through 1PS filter paper and concentrated under reduced pressure to give an oil. Distillation of the oil gave 101.5 g (62%) of the title compound, amide boiling at 197-202° C. (1 mm). The oil solidified on standing.

Provenance & Evidence