20594-83-6 Usage
Chemical Properties
Pale Yellow Solid
Originator
Nubain,Du Pont,US,1979
Uses
Different sources of media describe the Uses of 20594-83-6 differently. You can refer to the following data:
1. Nalbuphine is a mixed opioid agonist-antagonist. Nalbuphine is an analgesic (narcotic).
2. Mixed opioid agonist-antagonist. Analgesic (narcotic).
Manufacturing Process
To a slurry of 110.5 g of 14-hydroxydihydronormorphinone in 2.5 liters of
methylene chloride and 280 ml of triethylamine was added a solution of 106 g
of cyclobutanecarboxylic acid chloride in 500 ml of methylene chloride. The
temperature of the reaction mixture was maintained at 20°C to 25°C during
the addition. After 5 minutes the reaction mixture was brought to reflux and
heated for 5 hours.It was then cooled, washed with water, dried over sodium sulfate and
evaporated to dryness. The residue was crystallized from benzene and
pentane to give 138.5 g of the dicyclobutanecarbonyl derivative, melting point
about 112°C (dec.).The dicyclobutanecarbonyl derivative (136.7 g) was dissolved in 200 ml of
tetrahydrofuran and added dropwise to a suspension of 34.2 g of lithium
aluminum hydride in 1 liters of tetrahydrofuran. The temperature of the
mixture rose to reflux during the addition. Reflux was maintained for 2 hours
after the addition was completed. After cooling, 110 ml of ethyl acetate was
added dropwise, followed by 30 ml of water, followed by a solution of 53 g of
ammonium chloride in 125 ml of water. The resulting mixture was filtered and
the inorganic precipitate was washed with methanol. Evaporation of the
combined filtrates gave 66 g of N-cyclobutylmethyl-14-hydroxydihydronormorphinone, melting point 229°C to 231°C.
Brand name
Nubain (Endo).
Therapeutic Function
Analgesic
Check Digit Verification of cas no
The CAS Registry Mumber 20594-83-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,0,5,9 and 4 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 20594-83:
(7*2)+(6*0)+(5*5)+(4*9)+(3*4)+(2*8)+(1*3)=106
106 % 10 = 6
So 20594-83-6 is a valid CAS Registry Number.
InChI:InChI=1/C21H27NO4.ClH/c23-14-5-4-13-10-16-21(25)7-6-15(24)19-20(21,17(13)18(14)26-19)8-9-22(16)11-12-2-1-3-12;/h4-5,12,15-16,19,23-25H,1-3,6-11H2;1H/t15-,16+,19?,20-,21+;/m0./s1
20594-83-6Relevant articles and documents
Nalbuphine preparation method and intermediate thereof
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, (2021/05/08)
The invention discloses a nalbuphine preparation method and an intermediate thereof, and the nalbuphine is prepared by taking morphine as a raw material through acylation, catalytic oxidation, palladium/carbon hydrogenation reduction, N-methyl removal of chloroformic acid-1-chloroethyl ester, hydrolysis deprotection and nitrogen-methylcyclobutane substitution. According to the method, a chiral center is introduced from an initial raw material, in the whole reaction process, reactions and reagents which can influence the chiral center are not adopted, only conventional methods and equipment are used in the whole reaction process, and the method is easy and convenient to operate, mild in condition, short in route, high in overall yield and suitable for industrial production.
Preparation method of nalbuphine free alkali
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Paragraph 0010; 0033-0034, (2020/05/30)
The invention discloses a preparation method of nalbuphine free alkali, i.e., (-)-17-(cyclobutylmethyl)-4,5alpha-epoxymorphine-3,6alpha,14-hydroxyl. A synthetic route of the preparation method is shown in the specification. According to the novel method, a new reduction reaction condition is adopted, so the purity of nalbuphine free alkali in a reduction product reaches 99%, and the problems of excessive generation of 6-beta isomers of the reduction product and difficulty in purification of the free alkali are avoided.
CONVENIENT PREPARATION OF N-SUBSTITUTED MORPHINAN-6-OLS FROM MORPHINAN-6-ONES
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Paragraph 0095, (2015/05/13)
Described herein are methods of preparing 6-hydroxy N-alkyl morphinan-6-ols from morphinan-6-ones, as illustrated below: wherein the variables R1, R2, R3, R10, R11, R14, and are as defined herein and wherein the reactions occur in a one-pot procedure using a boron based reducing agent.
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