ChemicalBook CAS DataBase List Ropivacaine

Ropivacaine synthesis

8synthesis methods

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

98717-15-8

84057-95-4

The general procedure for the synthesis of (S)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide hydrochloride as raw material for the synthesis of (S)-N-(2,6-dimethylphenyl)-1-propyl-2-piperidine carboxamides was as follows: firstly, 1 g of (S)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide hydrochloride was dissolved in 35 g of USP-grade purified water . Subsequently, the pH was adjusted to 9-10 by slow dropwise addition of about 4 mL of 1.0 N sodium hydroxide solution.The precipitate precipitated from the reaction mixture was collected by filtration and washed with purified water. The resulting solid was re-dispersed in 50 mL of purified water, stirred for 15 min and filtered again and washed with purified water. After repeating the above dispersion, filtration and washing operations, the product was dried at 40 °C for 72 h to obtain the target compound (S)-N-(2,6-dimethylphenyl)-1-propyl-2-piperidine carboxamide.

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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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

98717-15-8
234 suppliers
$49.00/25mg

84057-95-4
221 suppliers
$49.00/10mg

References