ChemicalBook CAS DataBase List Medetomidine

Medetomidine synthesis

6synthesis methods

Product Name:Medetomidine
CAS Number:86347-14-0
Molecular formula:C13H16N2
Molecular Weight:200.28

Medetomidine is a synthetic compound used as a surgical anesthetic and analgesic. It is normally found as its hydrochloride salt, medetomidine hydrochloride. It was prepared from (R)-4-[1-(2,3-Dimethylphenyl)ethyl]-1H-imidazole hydrochloride with sodium hydroxide in water by stirring in acetone for 1h at 55 - 60℃.

86347-15-1 Synthesis

(R)-4-[1-(2,3-Dimethylphenyl)ethyl]-1H-imidazole hydrochloride

86347-15-1
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86347-14-0
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Yield:86347-14-0 89%

Reaction Conditions:

with sodium hydroxide in water;acetone at 55 - 60; for 1 h;

Steps:

Liberation and isolation of Medetomidine free base
Medetomidine x HCl, 783g, 3.31 mol, is dissolved in 2.5L water. Charcoal, 40g, is added and the mixture stirred for 30 minutes at 70°C. The charcoal is filtered and washed with 0.5L water. The combined filtrate and washing is diluted with 3.1 L acetone and 0.2L water. The temperature is adjusted to 55-60°C and a solution of 132g, 3.3 mol, sodium hydroxide in 0.54L water is added over ca 1h. The resulting emulsion is cooled to ca 40°C and crystallization is induced by seeding. The slurry is cooled to 0°C, filtered and the filter cake washed with 3 x 400 ml water. Drying under vacuum afforded 590g, 2.95 mol, 89%, of Medetomidine free base.

References:

CAMBREX KARLSKOGA AB;EKLUND, Lars;HANSSON, Lars;LUNDHOLM, Tommy;HOLMBERG, Pär;EEK, Margus WO2013/14428, 2013, A1 Location in patent:Page/Page column 37; 38

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