The Vespiary

The Hive => Tryptamine Chemistry => Topic started by: Lego on July 21, 2004, 06:30:00 PM

Title: Synthetic routes to dialkyltryptamines
Post by: Lego on July 21, 2004, 06:30:00 PM
Under construction

This digest should cover all synthetic methods leading to dialkyltryptamines, like DMT (dimethyltryptamine), DET (diethyltryptamine) and the like.













Molecule: (https://www.the-hive.ws/forum/faq.pl?Cat=#applet)

DMT ("c21ccccc1ncc2CCN(C)C")



Starting from indole












Molecule: (https://www.the-hive.ws/forum/faq.pl?Cat=#applet)

indole ("c21ccccc1ncc2")



Reaction with oxalyl chloride, amide formation with a dialkylamine, reduction with LAH:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/dmt.det.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/dmt.det.html)



Direct alkylation of indole grignards:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/dmt.indole.grignard.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/dmt.indole.grignard.html)



Reaction with chloroacetaldehyde and reduction with NaBH4:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/dmt.chloromethylgramine.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/dmt.chloromethylgramine.html)



Acetylation, bromination, dialkylamination, reduction:

https://www.thevespiary.org/rhodium/Rhodium/clandestine/dmt/index.html (https://www.thevespiary.org/rhodium/Rhodium/clandestine/dmt/index.html)


Post 451451 (https://www.thevespiary.org/talk/index.php?topic=13267.msg45145100#msg45145100)

(GC_MS: "Reduction of indolyl-3-aminomethylketones", Tryptamine Chemistry)

Post 451545 (https://www.thevespiary.org/talk/index.php?topic=13267.msg45154500#msg45154500)

(Chimimanie: "Thanks", Tryptamine Chemistry)

Post 475429 (https://www.thevespiary.org/talk/index.php?topic=13267.msg47542900#msg47542900)

(Vitus_Verdegast: "Old synthesis of DET via beta-keto-DET", Tryptamine Chemistry)

Starting from tryptamine












Molecule: (https://www.the-hive.ws/forum/faq.pl?Cat=#applet)

tryptamine ("c21ccccc1ncc2CCN")



Using HCHO/NaCNBH4 (sodium cyanoborohydride):

https://www.thevespiary.org/rhodium/Rhodium/chemistry/tryptamine2dmt.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/tryptamine2dmt.html)



Using HCHO/NaBH4:

Post 518988 (https://www.thevespiary.org/talk/index.php?topic=12949.msg51898800#msg51898800)

(Lego: "In defense of HCHO/NaBH4", Tryptamine Chemistry)

Using alkyliodides:

Post 126957 (https://www.thevespiary.org/talk/index.php?topic=12883.msg12695700#msg12695700)

(Lilienthal: "Breath of Hoax? / PTC tryptamine alkylation on the test bench", Tryptamine Chemistry)

https://www.thevespiary.org/rhodium/Rhodium/chemistry/tryptamine2dmt.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/tryptamine2dmt.html)




Starting from tryptophol












Molecule: (https://www.the-hive.ws/forum/faq.pl?Cat=#applet)

tryptophol ("c21ccccc1ncc2CCO")



With chloromethansulfonyl chloride/dimethylamine:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/tryptophol.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/tryptophol.html)



Starting from indoleacetic acid












Molecule: (https://www.the-hive.ws/forum/faq.pl?Cat=#applet)

indoleacetic acid ("c21ccccc1ncc2CC(=O)O")



N,N-Dialkylamide formation, reduction with LAH:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/indoleaceticacid.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/indoleaceticacid.html)




Starting from indoleacetonitrile












Molecule: (https://www.the-hive.ws/forum/faq.pl?Cat=#applet)

indoleacetonitrile ("c21ccccc1ncc2CC#N")



CuCl, dimethylamine, NaBH4:

Post 351772 (https://www.thevespiary.org/talk/index.php?topic=12580.msg35177200#msg35177200)

(Barium: "Nitriles to tertiary amines", Tryptamine Chemistry)


Starting from phenylhydrazine












Molecule: (https://www.the-hive.ws/forum/faq.pl?Cat=#applet)

phenylhydrazine ("c1ccccc1NN")



One step synthesis with 4-dimethylaminobutyraldehyde acetals:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/dmten.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/dmten.html)


Two step synthesis with 4-chlorobutanal/dimethylamine:

Post 388588 (https://www.thevespiary.org/talk/index.php?topic=12746.msg38858800#msg38858800)

(Rhodium: "DMT synthesis using 4-chlorobutanal", Tryptamine Chemistry)



Other methods

Post 447677 (https://www.thevespiary.org/talk/index.php?topic=12725.msg44767700#msg44767700)

(Rhodium: "DMT - As easy as ABC", Tryptamine Chemistry)

Post 381563 (https://www.thevespiary.org/talk/index.php?topic=12690.msg38156300#msg38156300)

(Rhodium: "Total synthesis of 5-MeO-DMT (50% overall yield!)", Tryptamine Chemistry)

Post 377548 (https://www.thevespiary.org/talk/index.php?topic=12957.msg37754800#msg37754800)

(Rhodium: "Solid-Phase Synthesis of 5-MeO-DMT (or DMT)", Tryptamine Chemistry)

Post 510951 (https://www.thevespiary.org/talk/index.php?topic=13168.msg51095100#msg51095100)

(Rhodium: "Novel route to dialkyltryptamines", Tryptamine Chemistry)


Precursors
Phenylhydrazine:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/phenylhydrazine.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/phenylhydrazine.html)


4-substituted butanals:

Post 388159 (https://www.thevespiary.org/talk/index.php?topic=12746.msg38815900#msg38815900)

(Rhodium: "4-Chlorobutanal", Tryptamine Chemistry)

Post 401468 (https://www.thevespiary.org/talk/index.php?topic=12746.msg40146800#msg40146800)

(Rhodium: "Synthesis of 4-Chlorobutanal and its derivatives", Tryptamine Chemistry)

Post 454558 (https://www.thevespiary.org/talk/index.php?topic=12746.msg45455800#msg45455800)

(Rhodium: "Prep of 4-Chlorobutanol from THF/HCl(aq)", Tryptamine Chemistry)

Post 476152 (https://www.thevespiary.org/talk/index.php?topic=12746.msg47615200#msg47615200)

(Rhodium: "Preparation of 4-halobutanal acetals", Tryptamine Chemistry)

Post 508707 (https://www.thevespiary.org/talk/index.php?topic=12746.msg50870700#msg50870700)

(Rhodium: "4-Aminobutanal Acetals + 5-MeO-Tryptamine", Tryptamine Chemistry)

Post 518714 (https://www.thevespiary.org/talk/index.php?topic=12746.msg51871400#msg51871400)

(Lego: "4-Dialkylaminobutyraldehyde acetals", Tryptamine Chemistry)

Post 456583 (https://www.thevespiary.org/talk/index.php?topic=13294.msg45658300#msg45658300)

(Vaillo: "A new route to 4-(N,N-dimethylamino)butanal", Tryptamine Chemistry)

https://www.thevespiary.org/rhodium/Rhodium/chemistry/dmten.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/dmten.html)


Tryptophol:

Post 427106 (https://www.thevespiary.org/talk/index.php?topic=13209.msg42710600#msg42710600)

(Chimimanie: "On tryptophol", Tryptamine Chemistry)

Post 435601 (https://www.thevespiary.org/talk/index.php?topic=12715.msg43560100#msg43560100)

(Rhodium: "Tryptophol from 3-Indoleglyoxyl chloride + NaBH4", Tryptamine Chemistry)

Post 435843 (https://www.thevespiary.org/talk/index.php?topic=12715.msg43584300#msg43584300)

(demorol: "Tryptophol from 3-indoleglyoxylyl chloride + LAH", Tryptamine Chemistry)
Dimethylamine:

Post 448644 (https://www.thevespiary.org/talk/index.php?topic=12648.msg44864400#msg44864400)

(Chimimanie: "Dimethylamine from formaline", Tryptamine Chemistry)

Post 513655 (https://www.thevespiary.org/talk/index.php?topic=6950.msg51365500#msg51365500)

(Vitus_Verdegast: "dimethylamine from hydrolysis of DMF", Chemistry Discourse)
3-Acetylindole:

Post 448820 (missing)

(Lego: "An improved method to obtain 3-acylindoles", Tryptamine Chemistry)
Tryptamine:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/tryptamine.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/tryptamine.html)


Post 507814 (https://www.thevespiary.org/talk/index.php?topic=12944.msg50781400#msg50781400)

(L42L: "novel newbee tryp decarb question session", Tryptamine Chemistry)

Post 416740 (https://www.thevespiary.org/talk/index.php?topic=13012.msg41674000#msg41674000)

(Rhodium: "Novel amino acid decarboxylation via the nitrile", Tryptamine Chemistry)

Post 369921 (https://www.thevespiary.org/talk/index.php?topic=12651.msg36992100#msg36992100)

(Cyrax: "Tryptamine from scratch", Tryptamine Chemistry)

Post 300317 (https://www.thevespiary.org/talk/index.php?topic=12589.msg30031700#msg30031700)

(PolytheneSam: "Tryptophan decarboxylation", Tryptamine Chemistry)

Post 361443 (https://www.thevespiary.org/talk/index.php?topic=13333.msg36144300#msg36144300)

(Rhodium: "Cyclohexanol decarboxylation of tryptophan", Tryptamine Chemistry)

Post 211603 (https://www.thevespiary.org/talk/index.php?topic=13266.msg21160300#msg21160300)

(Rhodium: "Another tryptophan decarboxylation", Tryptamine Chemistry)
Indol-3-yl-acetaldehyde:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/indoleacetaldehyde.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/indoleacetaldehyde.html)


Indoleacetic acid:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/iaa.synth.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/iaa.synth.html)


Post 324823 (https://www.thevespiary.org/talk/index.php?topic=13056.msg32482300#msg32482300)

(demorol: "indole-3-acetic acid synthesis", Tryptamine Chemistry)
Indoleacetonitrile:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/diethylaminoacetonitrile.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/diethylaminoacetonitrile.html)




Writeups of synthesis of precursors or/of dialkyltryptamines

Dimethylation of tryptamine:

Post 520556 (https://www.thevespiary.org/talk/index.php?topic=13094.msg52055600#msg52055600)

(dimitry: "DMT. NaBH4reduction", Tryptamine Chemistry)
Decarboxylation of tryptophan:

Post 507814 (https://www.thevespiary.org/talk/index.php?topic=12944.msg50781400#msg50781400)

(L42L: "novel newbee tryp decarb question session", Tryptamine Chemistry)