Gabapentin → HCID 68517401, compound

Participants

Reaction Steps

To a suspension of 3-bromomethylphenol (0.50 g, 2.67 mmol) in methylene chloride (8 ml), bis(trichloromethyl) carbonate (triphosgene, 0.368 g, 1.24 mmol) dissolved in methyl chloride (2 ml) and diisopropylethylamine (0.466 ml, 2.67 mmol) were cool added. The solution thus obtained was stirred one night at room temperature and then refluxed for 2 hours, This cooled solution was then dropped in a suspension of 1-(aminomethyl)cyclohexaneacetic acid (gabapentin, 0.911 g, 5.35 mmol) and diisopropylethylamine (0.932 ml, 5.35 mmol) in anhydrous dimethylformamide (4 ml). After 3 hours stirring, to the mixture ethyl acetate was added and it was washed with a 4% hydrochloric acid solution. The organic phase was dried under vacuum and the raw product thus obtained was purified by silica gel chromatography with n-hexane/ethyl acetate 1/1 (v/v) as eluent. The desired product was obtained as an oil (0.100 g) that was employed without further purification.

Provenance & Evidence