Pipecoloxylidide

Therapeutic Function Local anesthetic Chemical Name dl-1-butyl-2, 6 -pipecoloxylidide Common Name —... 

Disposition in the Body. Bupivacaine is metabolised in the liver by oxidative dealkylation to 2, 6 -pipecoloxylidide (PPX) 3 -and 4 -hydroxylation also occur. Less than 10% of a dose is excreted in the urine as unchanged drug in 24 hours. 

SYNS CHLOROCAIN N-(2,6-DIMETHYLPHENYL)-l-METHYL-2-PIPERIDINECARBOXAMIDE-MONO-HYDROCHLORIDE MEAVERIN MEPIVACAINE HYDROCHLORIDE dl-MEPIVACAINE HYDROCHLORIDE MEPIVASTESIN 1-METHYL-2, 6 -PIPECOLOXYLIDIDE HYDROCHLORIDE dl-1-METHYL-2, 6 -PIPECOLOXYLIDIDE HYDROCHLORIDE... 

Methyl-2, 6 -pipecoloxylidide monohydrochloride 2-Piperidinecarboxamide, N-(2, 6-dimethylphenyl)- -methyl-, monohydrochloride U.S.P. 

Simultaneous Determination of Bupi-vacaine and 2,6-Pipecoloxylidide in Serum by Gas-Liquid Chromatography... 

Pipecoloxylidide hydrochloride (1.0 kg), acetone (3.75 L), and water (0.85 L) were charged. NaOH (aq) was added to pH>ll. The phases, thus formed, were separated and the organic phase was diluted with water (1.4 L). L-(-)-Dibenzoyltartaric acid (0.67 kg), dissolved in acetone (3.75 L), was added. 

The solution was seeded. The crystal slurry was cooled to 2°C. The crystals were collected by centrifugation and were washed with acetone followed by isobutyl methyl ketone. The product was not dried. The moist crystalline product was extracted with isobutyl methyl ketone (3.60 L) and diluted NaOH (2.60 L) at pH>ll. The phases were separated. The organic phase was washed with water (0.6 L) and was used directly in the next step. Yield (calculated on the dry basis) about 0.39 kg of (S)-pipecoloxylidide (about. 90%). 

More recently, a procedure for the racemizatlon of pipecoloxylidide was developed by Backvall and coworkers [52]. Pipecoloxylidide is a pharmaceutical precursor of several local anesthetics of the amino amide group type. The (5)-enantiomer of these dmgs is the desired enantiomer since it shows high activity and is less toxic. It is therefore highly desirable to recycle the undesired (/ )-enantiomer to increase the overall efficiency of the process (Scheme 5). It was found that with 2 mol% of catalyst 1 in dibutyl ether at 140°C, enantiomerically pure pipecoloxylidide was almost completely racemized after 1 h (2% ee). 

---