Naloxone synthesis

14synthesis methods

Product Name:Naloxone
CAS Number:465-65-6
Molecular formula:C19H21NO4
Molecular Weight:327.37

Naloxone, (-)-17-(allyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-one (3.1.92), is synthesized by the alkylation of 14-hydroxydihydronormorphinane (3.1.82) by allylbromide [55–58].

33522-95-1 Synthesis

33522-95-1
83 suppliers
$60.60/013-1ml

106-95-6 Synthesis

106-95-6
424 suppliers
$10.00/5g

465-65-6
63 suppliers
$27.89/004-1ml

Yield:465-65-6 84%

Reaction Conditions:

with triethylamine in 1-methyl-pyrrolidin-2-one;water at 70; for 9.5 h;Inert atmosphere;

Steps:

7
Example 7; Naloxone Allyl bromide (56 mg; 0.463 mmol) and Et₃N (45 μl; 0.327 mmol) were added to a suspension of noroxymorphone (Example 5, 100 mg; 0.348 mmol) in a mixture of NMP/H₂O (10:1; 0.35 mL). The reaction vessel was purged with argon and the mixture was stirred at 70° C. for 2 h. At that time, additional Et₃N (45 μl; 0.327 mmol) was added and the mixture was stirred for an additional 7.5 h at 70° C. The reaction mixture was then cooled to room temperature, diluted with dichloromethane (15 mL), and washed with saturated NaHCO₃(3×3 mL). The aqueous layer was re-extracted with dichloromethane (5 mL) and the combined organic layers were dried over MgSO₄. Column chromatography of the residue (dichloromethane/methanol 4:1) afforded 96 mg (84%) of naloxone as a white solid mp: 181-182° C. (ethyl acetate), [lit. mp 173-175]^xix[lit. 179.5° C. (toluene)]^xxidentical in all respects to the material described in the literature.^xxi

References:

Brock University US2012/283443, 2012, A1 Location in patent:Page/Page column 18

FullText