Author Topic: Synthetic routes to dialkyltryptamines  (Read 2197 times)

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Lego

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Synthetic routes to dialkyltryptamines
« 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:

DMT ("c21ccccc1ncc2CCN(C)C")



Starting from indole












Molecule:

indole ("c21ccccc1ncc2")



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

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



Reaction with chloroacetaldehyde and reduction with NaBH4:

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



Acetylation, bromination, dialkylamination, reduction:

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


Post 451451

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

Post 451545

(Chimimanie: "Thanks", Tryptamine Chemistry)

Post 475429

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


Starting from tryptamine












Molecule:

tryptamine ("c21ccccc1ncc2CCN")



Using HCHO/NaCNBH4 (sodium cyanoborohydride):

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



Using HCHO/NaBH4:

Post 518988

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


Using alkyliodides:

Post 126957

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

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




Starting from tryptophol












Molecule:

tryptophol ("c21ccccc1ncc2CCO")



With chloromethansulfonyl chloride/dimethylamine:

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



Starting from indoleacetic acid












Molecule:

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



N,N-Dialkylamide formation, reduction with LAH:

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




Starting from indoleacetonitrile












Molecule:

indoleacetonitrile ("c21ccccc1ncc2CC#N")



CuCl, dimethylamine, NaBH4:

Post 351772

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



Starting from phenylhydrazine












Molecule:

phenylhydrazine ("c1ccccc1NN")



One step synthesis with 4-dimethylaminobutyraldehyde acetals:

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


Two step synthesis with 4-chlorobutanal/dimethylamine:

Post 388588

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




Other methods


Post 447677

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

Post 381563

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

Post 377548

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

Post 510951

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



Precursors
Phenylhydrazine:

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


4-substituted butanals:

Post 388159

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

Post 401468

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

Post 454558

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

Post 476152

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

Post 508707

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

Post 518714

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

Post 456583

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

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


Tryptophol:

Post 427106

(Chimimanie: "On tryptophol", Tryptamine Chemistry)

Post 435601

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

Post 435843

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

Dimethylamine:

Post 448644

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

Post 513655

(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


Post 507814

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

Post 416740

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

Post 369921

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

Post 300317

(PolytheneSam: "Tryptophan decarboxylation", Tryptamine Chemistry)

Post 361443

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

Post 211603

(Rhodium: "Another tryptophan decarboxylation", Tryptamine Chemistry)

Indol-3-yl-acetaldehyde:

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


Indoleacetic acid:

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


Post 324823

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

Indoleacetonitrile:

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




Writeups of synthesis of precursors or/of dialkyltryptamines

Dimethylation of tryptamine:

Post 520556

(dimitry: "DMT. NaBH4reduction", Tryptamine Chemistry)

Decarboxylation of tryptophan:

Post 507814

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