ChemicalBook CAS DataBase List Ropivacaine

Ropivacaine synthesis

8synthesis methods

Product Name:Ropivacaine
CAS Number:84057-95-4
Molecular formula:C17H26N2O
Molecular Weight:274.4

106-94-5 Synthesis

106-94-5
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(2S)-N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide)

27262-40-4
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84057-95-4
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$49.00/10mg

Yield:84057-95-4 94%

Reaction Conditions:

in tetrahydrofuran; for 20 - 24 h;Heating / reflux;

Steps:

1

Example 1. Preparation of Ropivacaine baseRopivacaine is prepared starting from the intermediate (S) pipecolic acid 2,6-xylidide (145 g; 0.624 mols) and n-propyl bromide (766 g; 6.24 mols) in tetrahydrofuran (2.5 L) under reflux for approx. 20-24 hours. Inorganic salts are filtered off and the solvent is evaporated to dryness to obtain a dry- solid, consisting of crude Ropivacaine base. The solid is taken up into the minimum amount of diisopropyl ether (200 ml) and filtered under vacuum. The residue is washed on the filter with the same solvent (3 x 150 ml) and dried at 55°C under vacuum to obtain 161 g of Ropivacaine base in a 94% molar yield on the xylidide; HPLC purity = 99.75%; HPLC enantiomeric purity = 99.54%, concentration = 99.5%; loss on drying: 0.3%. EPO The resulting product is a non-hygroscopic solid, that is stable in time and can be used for the formation of the hydrochloride in situ during the preparation of the pharmaceutical product.

References:

WO2006/133837,2006,A2 Location in patent:Page/Page column 3-4