Kemisk syntese af bupropion

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1. Abstract

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2. INDHOLDSFORTEGNELSE

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5.8.1. Erythrohydrobupropion og therohydrobupropion!4444!LA!

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4. PROJEKTBESKRIVELSE

4.1. Problemanalyse

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4.2. Problemformulering

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4.3. Tidsplan

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5. TEORI

5.1. Kemiske egenskaber

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5.2. Bupropion - historisk vinkel

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5.9. Noradrenalin

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6. INTRODUKTION TIL SYNTESE/ PRAKTISK ARBEJDE

6.1. Overordnet syntese

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6.2. Enhedsoperationer

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6.2.1. Omrøring

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6.2.2. Ekstraktion

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6.2.6 Inddampning

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6.3. Analyseværktøjer

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6.3.1. Smeltepunktsbestemmelse

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7.1.2. Fejlreaktioner

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RARY

7.1.3. Teoretiske beregninger

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Tabel 3: ("-%-3('(3-%(-!1&%!.-!0-&%-0')2-!7-%-3('(3-%!1'(.-)!'!"'+*3!L@4ZV!

7.1.4. Materialer

E L!3!,E=6+&%$%&$'&$6-(&$!

E S!,G!]'/6+&%,-06*(!

E !L[!,G!7_3-%3+*)!

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3GHF(#!T_#\F@GHA#EAZ@(A)L'G?CA(#FCIA(#&DC'A&A'(GC#!#

?%&/-)9!+-C(-.),'..-+9!)#(.6-.! ! !

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7-)0-,,-! C&+#,-(-0!*1!7%&,!.-%!)2*+!*(C-(.-)9!,-(!2#(!2-(.-%!2&(/-(0%*0'&(-(! *1!.-(!N()2-.-!

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,-.!-(!')&+-%-0!)0&1,_(3.-^!!

𝑐 = 𝑛/𝑉 ⇔ 𝑛 = 𝑐 ∗ 𝑉!

`'!2*(!(#!7-)0-,,-!,*))-(!#.!1%*!.-(!7-%-3(-!)0&1,_(3.-!&3!,&+*%,*))-(!1&%!.'7%&,9!)&,!-%!

LSZ9X[X!3p,&+4!!

𝑚 = 𝑛 ∗ 𝑀!

`-.!*0!7-(:00-!.-()'0-0-(!1&%!7%&,9!2*(!C'!(#!7-%-3(-!C&+#,-(!*1!7%&,!.-%!)2*+!*(C-(.-)!0'+!*0!+*C-!

LI!7%&,!&$+N)0!'!.'/6+&%,-06*(4!]-()'0-0-(!1&%!7%&,!-%!P9L[@X!3p,G!

𝜌 = 𝑚/𝑉! ⇔ 𝑉 = 𝑚/𝜌!

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,-06*(!0'+!C&+#,-(-0!-%!@[!,G4!!

7.1.5. Sikkerhed

/M&S 'CGCHA(!

:M&S 'CGCHA(!

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FP[@9!FPLY!

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(-)!7-0:.('(3!)-)!'!7'+*3!L@4S4!!

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)-)!'! 0*7-+! R 4!,E=6+&%$%&$'&$6-(&(!-%!-0! 2-,'2*+'-!)&,! -%!+'C)1*%+'30!C-.!'(.\(.'(3!&3!2*(! +'3-+-.-)!

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?%&/-)9!+-C(-.),'..-+9!)#(.6-.! ! !

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7.1.6. Fremgangsmåde

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&,%N%'(3!!

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%N%'(34!

A4 ]-)0'++g%!&$+N)('(3!'(.0'+!'(.6&+.-0!'!2&+7-(!'22-!2&3-%!

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7.2. Syntesetrin 2

7.2.1. Teoretisk forklaring bag syntesetrin

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0'&(!7+'C-%!-(!+-*C'(3!3%&# $!#. )2'10-0!, -. !-(!(#2 +-&1'+4!O(!(#2 +-& 1'+!7-0-3(- )!)&, !-0!,& +-2: +-9!.-%!

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)(*22-%!, *( !#(.-%!(#2 +-&1'+-!)#7 )0'0#0'&()%-*20'&(- %!& , !-(!THL!&3!TH@!%-*20'&(4!THL!%-*20'&(!-%!

L4!&%.-()!(#2+-&1'+-! )# 7) 0'0# 0'&( )% -* 20 '&( 9!)&, !1&% -3 \% !'!0&!0%'(^!KN%)0!1&% +*. -% !+-*C '(3 !3%& # $!-0!/* %E

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?%&/-)9!+-C(-.),'..-+9!)#(.6-.! ! !

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+-2:+-4!

KN+3-(.-!%-*20'&(!-%!):(0-)-0%'(!L!'!.*((-+)-( !*1!7 # $ %& $ '& ( ^!

3GHF(#!R_4A)L'G?CAC#? OA ( #&D C 'A & A' (G C#+#

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*1!.-00-^!

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7.3.5. Fremgangsmåde

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7.3.6. Resultater

Praktisk udbytte samt smeltepunktsbestemmelse !

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7.3.7. TLC analyse af hvert syntesetrin

7.3.8. Resultatbehandling

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7.3.9. Diskussion

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8. OPTIMERINGSFORSØG

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8.1. Optimeringsforsøg 1

8.1.1. Teoretisk begrundelse for optimering

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8.3.1. Teoretisk begrundelse for optimering

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8.3.5. Diskussion

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9. HOVEDFORSØG

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9.1. NMR analyse

9.1.1. NMR introduktion

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9.1.14. Konklusion

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9.2. Diskussion

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9.2.1. Miljømæssige overvejelser

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9.2.2. Diclhormethan

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9.2.3. Tert-butylamin

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9.2.4. N-methylpyrolidon

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9.2.5. Diethylether

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7&%0)2*11-)4!

9.2.6. Vurdering af bupropion

b.!1%*!.-(!1*%,*2&+&3')2!1&%2+*%'(3!*1!7#$%&$'&()!(-.7%:.-+)-! )*,0!-11-20! $\!.-!,&(&*,'(-!(-#E

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('(34!

12.6. Flowdiagram: Syntesetrin 1!

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12.7. Flowdiagram: Syntesetrin 2!

?%&/-)9!+-C(-.),'..-+9!)#(.6-.! ! !

T'.-!LL!*1!XX!!

12.8. Flowdiagram: Syntesetrin 3!

?%&/-)9!+-C(-.),'..-+9!)#(.6-.! ! !

T'.-!L@!*1!XX!!

12.9. Teoretisk masse beregning!

! !

?%&/-)9!+-C(-.),'..-+9!)#(.6-.! ! !

T'.-!LP!*1!XX!!

OCl !

𝑛(𝐶

𝐻

𝑂𝐶𝑙 ) =

𝑚(𝐶

𝐻

𝑂𝐶𝑙 )

𝑀(𝐶

𝐻

𝑂𝐶𝑙 )

𝑛(𝐶

𝐻

𝑂𝐶𝑙 ) =

168,62

𝑛(𝐶

𝐻

𝑂𝐶𝑙 ) = 0.006!𝑚𝑜𝑙 !

OBrCl!

𝑚(𝐶

𝐻

𝑂𝐵𝑟𝐶𝑙) = 𝑛(𝐶

𝐻

𝑂𝐶𝑙 ) ∗ 𝑀(𝐶

𝐻

𝑂𝐵𝑟𝐶𝑙)!

𝑚(𝐶

𝐻

𝑂𝐵𝑟𝐶𝑙) = 0. 006 ∗ 247,51!

𝑚(𝐶

𝐻

𝑂𝐵𝑟𝐶𝑙) = 1. 485!𝑔!

ONCl*HCl!

𝑚(𝐶

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𝐻

𝑂𝐶𝑙 ) ∗ 𝑀(𝐶

𝐻

𝑂𝑁𝐶𝑙 )!

𝑚(𝐶

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𝑂𝑁𝐶𝑙 ) = 0.006 ∗ 276.20!

𝑚(𝐶

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?%&/-)9!+-C(-.),'..-+9!)#(.6-.! ! !

T'.-!LR!*1!XX!!

11. Litteraturliste

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http://telstar.ote.cmu.edu/biology/supplements/functional-group/!

!https://www.caymanchem.com/app/template/Product.vm/catalog/10488 !

!https://www.caymanchem.com/app/template/Product.vm/catalog/10488!

!http://chromsci.oxfordjournals.org/content/50/5/433.long!

!http://www.fda.gov/ohrms/dockets/ac/04/briefing/b1-20-tab11A-Wellbutrin-Tabs-SLR028.pdf !

!http://www.emedexpert.com/facts/bupropion-facts.shtml!

https://www.sundhed.dk/borger/sygdomme-a-

aa/sundhedsoplysning/rygning/antirygemidler/antirygemedicin-bupropion/!

!http://www.medicinenet.com/bupropion/page2.htm!

!http://en.wikipedia.org/wiki/Tyrosine!

http://www.biotechacademy.dk/Undervisningsprojekter/Gymnasiale-

projekter/Laegemiddeludvikling/Teori/Funktionelle-grupper!

!https://www.caymanchem.com/app/template/Product.vm/catalog/9000522 !

!http://da.wikipedia.org/wiki/Serotonin#Syntese !

!http://www.webmd.com/smoking-cessation/bupropion-hydrochloride-zyban-for-quitting-smoking!

!http://da.wikipedia.org/wiki/Depression_%28psykisk%29 !

!http://www.ncbi.nlm.nih.gov/pmc/articles/PMC514842/ !

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!http://www.farma.ku.dk/index.php/Forsoeg-med-leverceller-kan-re/5972/0/!

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! http://www.rxmed.com/b.main/b2.pharmaceutical/b2.1.monographs/CPS-%20Monographs/CPS-

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!Hesse LM, Et al: CYP2B6 mediates the in vitro hydroxylation of bupropion: potential drug interactions

with other antidepressants, Department of pharmacology and experimental therapeutics (2000)

!http://www.mindandmuscle.net/articles/chemically-correct-bupropion-by-andrew-novick/!

!http://en.wikipedia.org/wiki/Bupropion

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