Detailed investigations into the Akabori–Momotani reaction for the synthesis of amphetamine type stimulants: Part 2
•Substituted benzaldehydes convert into pseudoephedrines.•Electronic influence of the substituent on reaction outcomes was minor.•Molecular modelling provides insight into substituents lack of influence.•Sub-optimal reaction conditions with p-methoxy benzaldehyde produce new by-products.•Stereochemi...
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| Veröffentlicht in: | Forensic science international 2018-06, Vol.287, p.207-216 |
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| creator | Doughty, David Kent, Emma Painter, Ben Pigou, Paul E. Johnston, Martin R. |
| description | •Substituted benzaldehydes convert into pseudoephedrines.•Electronic influence of the substituent on reaction outcomes was minor.•Molecular modelling provides insight into substituents lack of influence.•Sub-optimal reaction conditions with p-methoxy benzaldehyde produce new by-products.•Stereochemical purity of products rationalised by molecular modelling.
The Akabori–Momotani reaction can be used to synthesise pseudoephedrine in 50% yield from N-methylalanine and benzaldehyde. This paper investigates electronic effects of substituted benzaldehydes on the reaction to synthesise amphetamine type stimulants and identifies several new Akabori–Momotani by-products, 1-[(4-methoxybenzyl)(methyl)amino]ethanol (11c), 2-(4-methoxyphenyl)-3,4-dimethyl-1,3-oxazolidine (12c), 1,2,3,4-tetramethyl-5,6-di-(4-methoxyphenyl)piperazine (13c) and 1,2,4,5-tetramethyl-3,6-di-(4-methoxyphenyl)piperazine (14c). This paper also investigates pseudoephedrine and methamphetamine isomeric distribution from the Akabori–Momotani reaction with the aid of molecular modelling to understand why more pseudoephedrine than ephedrine is produced. |
| doi_str_mv | 10.1016/j.forsciint.2018.01.023 |
| format | Article |
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The Akabori–Momotani reaction can be used to synthesise pseudoephedrine in 50% yield from N-methylalanine and benzaldehyde. This paper investigates electronic effects of substituted benzaldehydes on the reaction to synthesise amphetamine type stimulants and identifies several new Akabori–Momotani by-products, 1-[(4-methoxybenzyl)(methyl)amino]ethanol (11c), 2-(4-methoxyphenyl)-3,4-dimethyl-1,3-oxazolidine (12c), 1,2,3,4-tetramethyl-5,6-di-(4-methoxyphenyl)piperazine (13c) and 1,2,4,5-tetramethyl-3,6-di-(4-methoxyphenyl)piperazine (14c). This paper also investigates pseudoephedrine and methamphetamine isomeric distribution from the Akabori–Momotani reaction with the aid of molecular modelling to understand why more pseudoephedrine than ephedrine is produced.</description><identifier>ISSN: 0379-0738</identifier><identifier>EISSN: 1872-6283</identifier><identifier>DOI: 10.1016/j.forsciint.2018.01.023</identifier><identifier>PMID: 29459189</identifier><language>eng</language><publisher>Ireland: Elsevier B.V</publisher><subject>Akabori-Momotani reaction ; Alcohol ; Amphetamines ; Benzaldehyde ; Byproducts ; Chemical synthesis ; Chemistry ; Clandestine synthesis ; Energy ; Ephedrine ; Ethanol ; Forensic sciences ; Investigations ; Laboratories ; Methamphetamine ; Molecular chains ; Molecular modelling ; Oxazolidine ; Piperazine ; Pseudoephedrine ; Stimulants</subject><ispartof>Forensic science international, 2018-06, Vol.287, p.207-216</ispartof><rights>2018 Elsevier B.V.</rights><rights>Copyright © 2018 Elsevier B.V. All rights reserved.</rights><rights>Copyright Elsevier Limited Jun 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c399t-50f1b1a38c8607f04407b6646041542a5d2177d1490b875a6aa9d808023532123</citedby><cites>FETCH-LOGICAL-c399t-50f1b1a38c8607f04407b6646041542a5d2177d1490b875a6aa9d808023532123</cites><orcidid>0000-0003-4341-4396</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.proquest.com/docview/2033244465?pq-origsite=primo$$EHTML$$P50$$Gproquest$$H</linktohtml><link.rule.ids>314,780,784,3548,27923,27924,45994,64384,64386,64388,72240</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29459189$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Doughty, David</creatorcontrib><creatorcontrib>Kent, Emma</creatorcontrib><creatorcontrib>Painter, Ben</creatorcontrib><creatorcontrib>Pigou, Paul E.</creatorcontrib><creatorcontrib>Johnston, Martin R.</creatorcontrib><title>Detailed investigations into the Akabori–Momotani reaction for the synthesis of amphetamine type stimulants: Part 2</title><title>Forensic science international</title><addtitle>Forensic Sci Int</addtitle><description>•Substituted benzaldehydes convert into pseudoephedrines.•Electronic influence of the substituent on reaction outcomes was minor.•Molecular modelling provides insight into substituents lack of influence.•Sub-optimal reaction conditions with p-methoxy benzaldehyde produce new by-products.•Stereochemical purity of products rationalised by molecular modelling.
The Akabori–Momotani reaction can be used to synthesise pseudoephedrine in 50% yield from N-methylalanine and benzaldehyde. This paper investigates electronic effects of substituted benzaldehydes on the reaction to synthesise amphetamine type stimulants and identifies several new Akabori–Momotani by-products, 1-[(4-methoxybenzyl)(methyl)amino]ethanol (11c), 2-(4-methoxyphenyl)-3,4-dimethyl-1,3-oxazolidine (12c), 1,2,3,4-tetramethyl-5,6-di-(4-methoxyphenyl)piperazine (13c) and 1,2,4,5-tetramethyl-3,6-di-(4-methoxyphenyl)piperazine (14c). This paper also investigates pseudoephedrine and methamphetamine isomeric distribution from the Akabori–Momotani reaction with the aid of molecular modelling to understand why more pseudoephedrine than ephedrine is produced.</description><subject>Akabori-Momotani reaction</subject><subject>Alcohol</subject><subject>Amphetamines</subject><subject>Benzaldehyde</subject><subject>Byproducts</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Clandestine synthesis</subject><subject>Energy</subject><subject>Ephedrine</subject><subject>Ethanol</subject><subject>Forensic sciences</subject><subject>Investigations</subject><subject>Laboratories</subject><subject>Methamphetamine</subject><subject>Molecular chains</subject><subject>Molecular modelling</subject><subject>Oxazolidine</subject><subject>Piperazine</subject><subject>Pseudoephedrine</subject><subject>Stimulants</subject><issn>0379-0738</issn><issn>1872-6283</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>8G5</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><sourceid>GUQSH</sourceid><sourceid>M2O</sourceid><recordid>eNqFkU1uFDEQhS1ERIbAFcASGzbdKf-72Y0S_qQgWMDacne7iYdpe7DdkWbHHXJDToKHSbJgg2SpZPmrV8_1EHpJoCVA5PmmnWLKg_ehtBSIboG0QNkjtCJa0UZSzR6jFTDVNaCYPkVPc94AgBBUPkGntOOiI7pboeXSFeu3bsQ-3Lhc_HdbfAy5XkvE5drh9Q_bx-R__7r9FOdYbPA4OTscKFxN_GXyPtSSfcZxwnbeXVfR2QeHy35XX4ufl60NJb_BX2wqmD5DJ5PdZvf8rp6hb-_efr340Fx9fv_xYn3VDKzrSiNgIj2xTA9agpqAc1C9lFwCJ4JTK0ZKlBoJ76DXSlhpbTdq0HUTglFC2Rl6fdTdpfhzqd8zs8-D21YzLi7ZUABFSD2ioq_-QTdxSaG6qxRjlHMuD5Q6UkOKOSc3mV3ys017Q8AckjEb85CMOSRjgJjqp3a-uNNf-tmND333UVRgfQRcXciNd8lUFRcGN_rkhmLG6P875A8M8qQd</recordid><startdate>201806</startdate><enddate>201806</enddate><creator>Doughty, David</creator><creator>Kent, Emma</creator><creator>Painter, Ben</creator><creator>Pigou, Paul E.</creator><creator>Johnston, Martin R.</creator><general>Elsevier B.V</general><general>Elsevier Limited</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7QP</scope><scope>7RV</scope><scope>7U7</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>8G5</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BHPHI</scope><scope>C1K</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>GUQSH</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>KB0</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M2O</scope><scope>M7P</scope><scope>MBDVC</scope><scope>NAPCQ</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>Q9U</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-4341-4396</orcidid></search><sort><creationdate>201806</creationdate><title>Detailed investigations into the Akabori–Momotani reaction for the synthesis of amphetamine type stimulants: Part 2</title><author>Doughty, David ; 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The Akabori–Momotani reaction can be used to synthesise pseudoephedrine in 50% yield from N-methylalanine and benzaldehyde. This paper investigates electronic effects of substituted benzaldehydes on the reaction to synthesise amphetamine type stimulants and identifies several new Akabori–Momotani by-products, 1-[(4-methoxybenzyl)(methyl)amino]ethanol (11c), 2-(4-methoxyphenyl)-3,4-dimethyl-1,3-oxazolidine (12c), 1,2,3,4-tetramethyl-5,6-di-(4-methoxyphenyl)piperazine (13c) and 1,2,4,5-tetramethyl-3,6-di-(4-methoxyphenyl)piperazine (14c). This paper also investigates pseudoephedrine and methamphetamine isomeric distribution from the Akabori–Momotani reaction with the aid of molecular modelling to understand why more pseudoephedrine than ephedrine is produced.</abstract><cop>Ireland</cop><pub>Elsevier B.V</pub><pmid>29459189</pmid><doi>10.1016/j.forsciint.2018.01.023</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0003-4341-4396</orcidid></addata></record> |
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| ispartof | Forensic science international, 2018-06, Vol.287, p.207-216 |
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| source | Elsevier ScienceDirect Journals Complete - AutoHoldings; ProQuest Central UK/Ireland |
| subjects | Akabori-Momotani reaction Alcohol Amphetamines Benzaldehyde Byproducts Chemical synthesis Chemistry Clandestine synthesis Energy Ephedrine Ethanol Forensic sciences Investigations Laboratories Methamphetamine Molecular chains Molecular modelling Oxazolidine Piperazine Pseudoephedrine Stimulants |
| title | Detailed investigations into the Akabori–Momotani reaction for the synthesis of amphetamine type stimulants: Part 2 |
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