Über die Einwirkung von Oxalsäure auf Kodein. XIII. Mitteilung zur Kenntnis des Morphins von Ludwig Knorr

Knorr, Ludwig; Roth, Paul

doi:10.1002/cber.190704003108

Cited by 12 publications

(2 citation statements)

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“…It is reasonable to assume that apocodeine (apomorphine 3-methyl ether, known as pseudoapocodeine in early publications) is formed from codeine by a mechanism similar to that which we propose for apomorphine. This assumption receives some support in Knorr's observation (15) that a better yield of apocodeine is obtained from pseudocodeine (in which the first step, an a, 7-shift, has already taken place) than from codeine. The usual preparative methods have consisted in melting codeine with oxalic acid or zinc chloride.…”

Section: Polyhalogen Derivatives the Mechanism Of Apomorphine Formationmentioning

confidence: 85%

THE HALOGENO-MORPHIDES AND -CODIDES, AND THE MECHANISM OF THE MORPHINE-APOMORPHINE TRANSFORMATION¹

Small¹,

Faris²,

Mallonee³

1940

J. Org. Chem.

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The halogenomorphides and halogendcodides are formed when the secondary alcoholic hydroxyl group of morphine or codeine is replaced by a halogen atom. Although the compounds occupy a position of considerable importance in the development of the morphine structural theory, and are the source of the morphine and codeine isomers, there has been no direct proof of structure offered for any single member of the series.The related pair, -chloromorphide and -chlorocodide, are the principal products obtained when morphine and codeine, respectively, are treated with thionyl chloride or phosphorus pentachloride. The halogen atom has tacitly been assumed to take the place of the hydroxyl that is known to occupy the 6-position, although it has been shown (1,2,3) in recent years that replacement of a group at this point in the nucleus often involves an a,7-shift, as a result of which the new group may appear at position 8. In carrying out numerous kilogram-scale preparations, we have observed that the a compounds are not the only products of the reaction, but are accompanied by the ß-halogeno derivatives to the extent of 10% to 15% of the total yield. In the codeine series, a-and 0-chlorocodides were obtained in part in the form of a new molecular compound of constant properties, that could not be separated into the components by fractional crystallization, although a-and ß-chlorocodides themselves differ considerably in solubility. Separation through salts, a method previously employed successfully for similar molecular compounds in the 1 The work reported in this paper is part of a unification of effort by a number of agencies having responsibility for the solution of the problem of drug addiction.

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Section: Polyhalogen Derivatives the Mechanism Of Apomorphine Formationmentioning

confidence: 85%

THE HALOGENO-MORPHIDES AND -CODIDES, AND THE MECHANISM OF THE MORPHINE-APOMORPHINE TRANSFORMATION¹

Small¹,

Faris²,

Mallonee³

1940

J. Org. Chem.

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“…«-Chloro-. 'S,4-dimethoxy-2-nitrotoluene (7). 19 (70 g, 0.33 mol) was converted into the corresponding benzyl chloride by reaction with 700 ml of concentrated HC1 during 2.5 hr.…”

Section: -Nitroveratryl Alcohol (19)mentioning

confidence: 99%

Aporphines. 8. Total Synthesis and Pharmacological Evaluation of (±)-Apomorphine, (±)-Apocodeine, (±)-N-n-Propylnorapomorphine, and (±)-N-n--Propylnorapocodeine

Neumeyer¹,

Neustadt²,

Oh³

et al. 1973

J. Med. Chem.

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Über das Allopseudokedein, ein neues isomeres des Kodeins. XIV. Mitteilung zur Kenntnis des Morphins von Ludwig Knorr

Knorr¹,

Hörlein²,

Grimme³

1907

Ber. Dtsch. Chem. Ges.

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Über die Einwirkung von Oxalsäure auf Kodein. XIII. Mitteilung zur Kenntnis des Morphins von Ludwig Knorr

Cited by 12 publications

References 2 publications

THE HALOGENO-MORPHIDES AND -CODIDES, AND THE MECHANISM OF THE MORPHINE-APOMORPHINE TRANSFORMATION¹

THE HALOGENO-MORPHIDES AND -CODIDES, AND THE MECHANISM OF THE MORPHINE-APOMORPHINE TRANSFORMATION¹

Aporphines. 8. Total Synthesis and Pharmacological Evaluation of (±)-Apomorphine, (±)-Apocodeine, (±)-N-n-Propylnorapomorphine, and (±)-N-n--Propylnorapocodeine

Über das Allopseudokedein, ein neues isomeres des Kodeins. XIV. Mitteilung zur Kenntnis des Morphins von Ludwig Knorr

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Über die Einwirkung von Oxalsäure auf Kodein. XIII. Mitteilung zur Kenntnis des Morphins von Ludwig Knorr

Cited by 12 publications

References 2 publications

THE HALOGENO-MORPHIDES AND -CODIDES, AND THE MECHANISM OF THE MORPHINE-APOMORPHINE TRANSFORMATION1

THE HALOGENO-MORPHIDES AND -CODIDES, AND THE MECHANISM OF THE MORPHINE-APOMORPHINE TRANSFORMATION1

Aporphines. 8. Total Synthesis and Pharmacological Evaluation of (±)-Apomorphine, (±)-Apocodeine, (±)-N-n-Propylnorapomorphine, and (±)-N-n--Propylnorapocodeine

Über das Allopseudokedein, ein neues isomeres des Kodeins. XIV. Mitteilung zur Kenntnis des Morphins von Ludwig Knorr

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THE HALOGENO-MORPHIDES AND -CODIDES, AND THE MECHANISM OF THE MORPHINE-APOMORPHINE TRANSFORMATION¹

THE HALOGENO-MORPHIDES AND -CODIDES, AND THE MECHANISM OF THE MORPHINE-APOMORPHINE TRANSFORMATION¹