AU2021106875A4 - A method of synthesizing a compound - Google Patents
A method of synthesizing a compound Download PDFInfo
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- AU2021106875A4 AU2021106875A4 AU2021106875A AU2021106875A AU2021106875A4 AU 2021106875 A4 AU2021106875 A4 AU 2021106875A4 AU 2021106875 A AU2021106875 A AU 2021106875A AU 2021106875 A AU2021106875 A AU 2021106875A AU 2021106875 A4 AU2021106875 A4 AU 2021106875A4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a method of synthesizing alkylamphetamine
analogues and intermediates thereof. The present invention provides an
effective and efficient method to synthesize alkylamphetamine analogues and
5 intermediates thereof.
Description
A method of synthesizing a compound
[0001] The present invention relates to the field of chemical compounds. More particularly, the present invention relates to a method of synthesizing compounds. Even more particularly, the present invention relates to a method of synthesizing alkylamphetamine analogues or derivatives and intermediates thereof.
[0002] Any reference to background art herein is not to be construed as an admission that such art constitutes common general knowledge in Australia or elsewhere.
[0003] Amphetamines are a central nervous system stimulant that can be utilized in the treatment of certain disorders. These disorders include attention deficit hyperactive disorder (ADHD), narcolepsy and obesity.
[0004] Certain alkylamphetamines are postulated to be useful in psychotherapy for post-traumatic stress disorder (PTSD). In this regard, it is postulated that the administration of alkylamphetamine to a subject undergoing psychotherapy may enhance the treatment thereof.
[0005] Presently, methods of synthesizing alkylamphetamine analogues or derivatives are convoluted and result in a generally poor yield. In this regard, the number of chemical reactions required to access the alkylamphetamine can be quite large and complicated. Furthermore, some of these methods utilize expensive reagents which adds to the overall cost of synthesis.
[0006] It would be advantageous to address one or more of the above issues, or to at least provide the consumer with a commercial alternative.
[0007] In a first aspect, although it need not be the only or indeed the broadest aspect, the invention resides a method of preparing a compound of formula (1)
R3 RSRHRio
R2 R11 R9 R 7 R12
wherein X and Y are independently selected from 0, N or C,
R1-R12 are each independently selected from the group consisting of H or alkyl; the method including the steps of completing a reductive amination reaction on a compound of Formula (IV)
R3 R5R R1 X ' NH2 R2 -( R8 RY R7 R4 (IV)
using an aldehyde or aldehyde derivative, catalyst and hydrogen gas; or
using aldehyde or aldehyde derivative and dimethylsulfate; or
using alkylcarboxylic acid and a reducing agent; or
using aldehyde or aldehyde derivative and a reducing agent; or
using an alkylhalide and a base.
[0008] In one embodiment, the aldehyde or aldehyde derivative is paraformaldehyde or formaldehyde.
[0009] In some embodiments, the catalyst is platinum oxide. In one embodiment, the platinum oxide is PtO2.
[0010] In one embodiment, the alkylcarboxylic acid is formic acid. In an embodiment, the reducing agent is lithium aluminium hydride, or aluminium amalgam.
[0011] In one embodiment, the alkylhalide is methylhalide. I an embodiment, the base is cesium hydroxide.
[0012] In one embodiment, the compound of formula (1) is 3,4-Methyl enedioxymethamphetamine.
[0013] In one embodiment, the compound of formula (IV) is formed by the method of second aspect.
[0014] In a second aspect, the invention resides in a method of preparing a compound of formula (IV)
R3 R5R R, X r NH 2 R2 -( Rg R9 R7 R4 (IV)
wherein X and Y are independently selected from 0, N or C,
R1-R9 are each independently selected from the group consisting of H or alkyl; the method including the steps of reacting a compound of Formula (III)
R3 R5 R RIX NH2 R2 R Ri 2 R9 R7 R4 iI
with a halogen and base.
[0015] In an embodiment, the halogen is selected from the group consisting of fluorine, chlorine, bromine and iodine. In a preferred embodiment, the halogen is bromine.
[0016] In some embodiments, the base is hydroxide. In one embodiment, the base is sodium hydroxide and/or potassium hydroxide.
[0017] In one embodiment, the compound of formula (III) is formed by the method of third aspect.
[0018] In a third aspect, the invention resides in a method of preparing a compound of formula (III)
R3 R5 R6
RX N NH2 R2 R Ra 2 Y- R9 R7 R4||)
wherein X and Y are independently selected from 0, N or C,
R1-R9 are each independently selected from the group consisting of H or alkyl; the method including the steps of reacting a compound of Formula (II)
R3 RSR
R2 Ra3 R9 R7 R4 (II) (
with hydroxylamine in a solvent followed by a base and an oxidizing agent; or
with a solvent and a salt.
[0019] In embodiments, the solvent is dimethyl sulfoxide, an alcohol, and/or aromatic hydrocarbon(s). In one embodiment, the alcohol is methanol and/or ethanol. In some embodiments, the aromatic hydrocarbon is benzene, toluene and/or xylene.
[0020] In one embodiment, the hydroxylamine is hydroxylamine hydrochloride.
[0021] In some embodiments, the base is a hydroxide, a carbonate and/or acetate. In one embodiment, the base is sodium carbonate, sodium acetate, sodium hydroxide and/or potassium hydroxide.
[0022] In one embodiment, the oxidizing agent is hydrogen peroxide.
[0023] In embodiments, the salt is a metal salt. In some embodiments, the metal salt is or is in the form of nickel acetate, zinc oxide, copper (II)sulphate, copper (III) sulphate
[0024] In one embodiment, the compound of Formula (II) is commercially obtained. In one embodiment the compound of Formula (II) is helional.
[0025] In one aspect, the invention resides in a compound of formula (1) formed by the method of the first aspect
R3 RSRHRIO
R2 -AR R1 R9 R7 R R4 (I).
[0026] In one embodiment, the invention resides in the use of a compound of formula (1) formed by the method of the first aspect in psychotherapy. In some embodiments, psychotherapy includes but is not limited to treatment of PTSD, ADHD autism, anxiety, depression and/or addiction. Furthermore it is postulated that a compound of formula (1) formed by the method of the first aspect can be utilized in couples counselling.
[0027] In one embodiment, the invention resides in the use a compound of formula (1) formed by the method of the first aspect in micro-dosing as a non psychotherapeutic use.
[0028] In an embodiment of the first to third aspects, the alkyl is a C1-C4 alkyl.
[0029] In some embodiment of the first to third aspects, R, R2, R3, R3, R4, R 5, R6, R7, R8, R9, R1o, Ri1, R12, where applicable, are all H.
[0030] In one embodiment of the first to third aspects, X is 0.
[0031] In embodiments of the first to third aspects, Y is O.
[0032] The various features and embodiments of the present invention referred to in the individual sections above and in the description which follows apply, as appropriate, to other sections, mutatis mutandis. Consequently, features specified in one section may be combined with features specified in other sections as appropriate.
[0033] Further features and advantages of the present invention will become apparent from the following detailed description.
[0034] Embodiments of the present invention reside primarily in a method of synthesizing alkylamphetamine analogues or derivatives and intermediates thereof. Accordingly, the method steps have been illustrated in concise schematic form in the drawings, showing only those specific details that are necessary for understanding the embodiments of the present invention so as to not obscure the disclosure with excessive detail that will be readily apparent to those of ordinary skill in the art having the benefit of the present description.
[0035] In this specification, adjectives such as first and second, left and right, and the like may be used solely to distinguish one element or action from another element or action without necessarily requiring or implying any actual such relationship or order.
[0036] Words such as "comprises" or "includes" are intended to define a non exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed, including elements that are inherent to such a process, method, article, or apparatus.
[0037] As used herein, the term 'about' means the amount is nominally the number following the term 'about' but the actual amount may vary from this precise number to an unimportant degree.
[0038] The present invention is predicated on the finding that alkylamphetamine analogues and intermediates thereof can be easily accessed by the present method. The inventors have found that the present method allows for a much easier synthesis of alkylamphetamine analogues or derivatives and intermediates thereof.
[0039] In a first aspect, although it need not be the only or indeed the broadest aspect, the invention resides in a method of preparing a compound of formula (1)
R3 RSRHRIO R R11 R2 - / IR8 -RR9 RR1 R 2 7 R4 (I),
wherein X and Y are independently selected from 0, N or C,
R1-R 12 are each independently selected from the group consisting of H or alkyl; the method including the steps of completing a reductive amination reaction on a compound of Formula (IV)
R3 R5R R1 X RNH2 R2 - I Rs Y -®R 9 R7 R4 (IV)
using an aldehyde or aldehyde derivative, catalyst and hydrogen gas; or
using aldehyde or aldehyde derivative and dimethylsulfate; or
using alkylcarboxylic acid and a reducing agent; or
using aldehyde or aldehyde derivative and a reducing agent; or
using an alkylhalide and a base.
[0040] In one embodiment, the aldehyde or aldehyde derivative is paraformaldehyde or formaldehyde.
[0041] In some embodiments, the catalyst is platinum oxide. In one embodiment, the platinum oxide is PtO2.
[0042] In one embodiment, the alkylcarboxylic acid is formic acid. In an embodiment, the reducing agent is lithium aluminium hydride, or aluminium amalgam.
[0043] In one embodiment, the alkylhalide is methylhalide. I an embodiment, the base is cesium hydroxide.
[0044] In one embodiment, the compound of formula (IV) is formed by the method of second aspect.
[0045] In a second aspect, the invention resides in a method of preparing a compound of formula (IV)
R1 X R RNH2 R2 Rs Y R9 R7 R4(IV)
wherein X and Y are independently selected from 0, N or C,
R1-R9 are each independently selected from the group consisting of H or alkyl; the method including the steps of reacting a compound of Formula (III)
R3 RR 5 0
R2 I RNH2 Y--y R9 R7 R4 ii
with a halogen and base.
[0046] In an embodiment, the halogen is selected from the group consisting of fluorine, chlorine, bromine and iodine. In a preferred embodiment, the halogen is bromine.
[0047] In some embodiments, the base is hydroxide. In one embodiment, the base is sodium hydroxide and/or potassium hydroxide.
[0048] In one embodiment, the compound of formula (III) is formed by the method of third aspect.
[0049] In a third aspect, the invention resides in a method of preparing a compound of formula (III)
R3 R5 0
R2 R 8 NH2 YY ~R 9 R7 R4 gi
wherein X and Y are independently selected from 0, N or C,
R1-R are each independently selected from the group consisting of H or alkyl; the method including the steps of reacting a compound of Formula (II)
R3 RSR R1 X R Ns R2 R8 R9 R7 (II)
with hydroxylamine in a solvent followed by a base and an oxidizing agent; or
with a solvent and a salt.
[0050] In embodiments, the solvent is dimethyl sulfoxide, an alcohol, or aromatic hydrocarbon(s). In one embodiment, the alcohol is methanol or ethanol. In some embodiments, the aromatic hydrocarbon is benzene, toluene and/or xylene.
[0051] In one embodiment, the hydroxylamine is hydroxylamine hydrochloride.
[0052] In some embodiments, the base is a hydroxide, a carbonate and/or acetate. In one embodiment, the base is sodium carbonate, sodium acetate, sodium hydroxide and/or potassium hydroxide.
[0053] In one embodiment, the oxidizing agent is hydrogen peroxide.
[0054] In embodiments, the salt is a metal salt. In some embodiments, the metal salt is or is in the form of nickel acetate, zinc oxide, copper (II)sulphate, copper (III) sulphate
[0055] In one embodiment, the compound of Formula (II) is commercially obtained. In one embodiment the compound of Formula (II) is helional.
[0056] In one aspect, the invention resides in a compound of formula (1) formed by the method of the first aspect
R3 RSRHRio
r R11 R2 RaR R9 R 7 R12 R4 (I).
[0057] In one embodiment, the invention resides in the use of a compound of formula (1) formed by the method of the first aspect in psychotherapy. In some embodiments, psychotherapy includes but is not limited to treatment of PTSD, ADHD autism, anxiety, depression and/or addiction. Furthermore it is postulated that a compound of formula (1) formed by the method of the first aspect can be utilized in couples counselling.
[0058] In one embodiment, the invention resides in the use a compound of formula (1) formed by the method of the first aspect in micro-dosing as a non psychotherapeutic use.
[0059] In an embodiment of the first to third aspects, the alkyl is a C1-C4 alkyl.
[0060] In some embodiment of the first to third aspects, R, R2, R3, R3, R4, Rs, R6, R7, R8, R9, R1o, Ri1, R12, where applicable, are all H.
[0061] In one embodiment of the first to third aspects, X is 0.
[0062] In embodiments of the first to third aspects, Y is O.
[0063] In one embodiment, the compound of formula (1) is 3,4-Methyl enedioxymethamphetamine.
[0064] It should be clear that the present invention substantially reduces the number of synthetic steps required to obtain an alkylamphetamine. The present invention allows for a number of alkylamphetamines to be accessed easily and efficiently.
Experimental
[0065] To a flask was charged helional (1 mol), ethanol (8.34 mol), hydroxylamine hydrochloride (1.79 mol), NaCO3 (0.73 mol) and water (10.67 mol). The resultant mixture formed 2-methyl-3-(3,4-methylenedioxyphenyl)prop 1-ylidene-hydroxylamine (MMDPPHA).
[0066] To a flask was charged MMDPPHA (1 mol), xylene (0.43 mol) and nickel acetate (0.02 mol). The resultant mixture formed 2-methyl-3-(3,4 methylenedioxyphenyl)propanamide (MMDPPA).
[0067] To a flask was charged MMDPPA (1 mol), sodium hydroxide (+ 2.4 mol), water (100 mol) and 4.2% sodium hypochlorite (153.7 mol). The resultant mixture formed 3,4-methylenedioxyamphetamine (MDA).
[0068] To a flask was charged MDA (1 mol), formic acid (16.4 mol) and benzene (46.03 mol). The resultant mixture formed N-formyl-MDA (FMDA).
[0069] To a flask was charged FMDA (1 mol), tetrahydrofuran (207.14 mol) and lithium aluminium hydride (5.25 mol). The resultant mixture formed 3,4 methylenedioxymethamphetamine (MDMA).
[0070] The above description of various embodiments of the present invention is provided for purposes of description to one of ordinary skill in the related art. It is not intended to be exhaustive or to limit the invention to a single disclosed embodiment. As mentioned above, numerous alternatives and variations to the present invention will be apparent to those skilled in the art of the above teaching.
[0071] Accordingly, while some alternative embodiments have been discussed specifically, other embodiments will be apparent or relatively easily developed by those of ordinary skill in the art. Accordingly, this invention is intended to embrace all alternatives, modifications and variations of the present invention that have been discussed herein, and other embodiments that fall within the spirit and scope of the above described invention.
Claims (5)
1. A method of preparing a compound of Formula (1)
R3 RSRHRIO /~X ,N R1 R2 R R y R0 R R R 12 9 7 R4 (I), wherein X and Y are independently selected from 0, N or C,
R1-R12 are each independently selected from the group consisting of H or alkyl; the method including the steps of completing a reductive amination reaction on a compound of Formula (IV)
R3 RS R1 X m6 NH2 R2 -< Rs YD R9 R7 R4 (IV)
using an aldehyde or aldehyde derivative, catalyst and hydrogen gas; or
using an aldehyde or aldehyde derivative and dimethylsulfate;
using an aldehyde or aldehyde derivative, catalyst and hydrogen gas; or
using aldehyde or aldehyde derivative and dimethylsulfate; or
using alkylcarboxylic acid and a reducing agent; or
using aldehyde or aldehyde derivative and a reducing agent; or
using an alkylhalide and a base.
2. The method of claim 1, wherein the compound of Formula (IV) is prepared by reacting a compound of Formula (III)
R3 R5 0 R1 X NH2 R2 I R8 Y R9 R7 R4
with a halogen and base.
3. The method of claim 2, wherein the compound of Formula (Ill) is prepared by reacting a compound of Formula (II)
R3 R5 R1 RX R 0 R2 R8 YC R9 R7 R4
with hydroxylamine in a solvent followed by a base and an oxidizing agent; or
with a solvent and a salt.
4. The method of any one of the preceding claims, wherein R, R2, R3, R3, R4, R 5, R6, R 7, R8, R9, R10, R1, R12, where applicable, are H; and wherein X and Y are 0.
5. A compound of Formula (1) produced by the method of any one of the preceding claims.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2021106875A AU2021106875A4 (en) | 2021-08-24 | 2021-08-24 | A method of synthesizing a compound |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2021106875A AU2021106875A4 (en) | 2021-08-24 | 2021-08-24 | A method of synthesizing a compound |
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| Publication Number | Publication Date |
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| AU2021106875A4 true AU2021106875A4 (en) | 2021-11-25 |
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Free format text: THE NATURE OF THE AMENDMENT IS: AMEND THE NAME TO DELETE THE PATENTEE MICHAEL BUCK IP |
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Owner name: OCTAVIAN & DESMOND PTY LTD Free format text: FORMER NAME(S): MICHAEL BUCK IP; OCTAVIAN & DESMOND PTY LTD |