Post 8809 (https://www.thevespiary.org/talk/index.php?topic=12952.msg880900#msg880900)
(Lilienthal: "Re: maybe 4 steps from tryptophan to DMT/DET/DPT", Tryptamine Chemistry):Patent US2692882 (http://l2.espacenet.com/dips/viewer?PN=US2692882&CY=gb&LG=en&DB=EPD)
5-benzyloxy-indole-3-acetamidesPatent US2703325 (http://l2.espacenet.com/dips/viewer?PN=US2703325&CY=gb&LG=en&DB=EPD)
5-benzyloxy-indole-3-acetonitriles __> 5-benzyloxy-tryptaminesPatent US2728778 (http://l2.espacenet.com/dips/viewer?PN=US2728778&CY=gb&LG=en&DB=EPD)
5-benzyloxy-indole-3-acetonitrilesPatent US1793176 (http://l2.espacenet.com/dips/viewer?PN=US1793176&CY=gb&LG=en&DB=EPD)
(2-methyl indole MgX (grignard reagent) reacted with ClCH2CH2N(CH3)2 to get 2-methyl DMT; example 6).Patent US4017513 (http://l2.espacenet.com/dips/viewer?PN=US4017513&CY=gb&LG=en&DB=EPD)
looks interesting. I wonder if it could work for IAA and dimethylamine.Patent US4017513 (http://l2.espacenet.com/dips/viewer?PN=US4017513&CY=gb&LG=en&DB=EPD)
Patent US6291712 (http://l2.espacenet.com/dips/viewer?PN=US6291712&CY=gb&LG=en&DB=EPD)
In addition to the above processes, a process for producing a carboxylic acid amide has been proposed, in which the
carboxylic acid amide is produced from an ammonium carboxylate in the presence of a dehydration catalyst. In this process,
molybdenum oxide, an alkyltin catalyst, a mixture of silica gel and alumina or a titanium tetrachloride catalyst is used as the
dehydration catalyst.
In this process, the dehydration reaction can be carried out at relatively low temperatures, so that not only can the formation of
by-products such as nitrile compounds and carboxylic acid amide dimerization products be suppressed but also the reaction
time can be shortened. However, when the carboxylic acid amide is produced with the use of the catalyst, it is apprehended
that the catalyst be dissolved or otherwise contained in the obtained carboxylic acid amide and, hence, a step of separating or
otherwise removing the catalyst from the carboxylic acid amide after the completion of the reactions becomes requisite. If costs
of catalyst production and catalyst removal incurred by the use of the catalyst, etc. are taken into account, this process also
cannot be regarded as a satisfactory process.
Patent US4379928 (http://l2.espacenet.com/dips/viewer?PN=US4379928&CY=gb&LG=en&DB=EPD)
Alkyl amides have been synthesized from cyclic anhydrides, carboxyl acids and their esters by contacting them with an amine carbamic acid salt.
The amine carbamic acid salts can be prepared by the interaction, e.g., of an alkylamine and carbon dioxide. A suitable
procedure is described in U.S. Pat. No. 2,927,128 by H. A. Lindahl et al. assignors to Pure Oil Co.
Alternately the amine carbamic acid salts can be generated in situ by the reaction of carbon dioxide with an amine. In the simple
case where the amine is dimethyl amine, the equation for the reaction is: ##STR7##
Patent US6313294 (http://l2.espacenet.com/dips/viewer?PN=US6313294&CY=gb&LG=en&DB=EPD)
Many conventional synthetic pathways exist for preparing amide compounds. For instance, the reaction of an amine and an
ester in a solvent, a well-known basic organic reaction, can be used to form an amide. In particular, it is known that the
formation of an amide linkage by the reaction of a primary amine with an ester in a solvent under heating is possible. Moreover,
the formation of an amide by reacting a secondary amine and an ester, can require not only a solvent, but also a catalyst, such
as Lewis acid, strong base, or enzyme.
Patent US3763234 (http://l2.espacenet.com/dips/viewer?PN=US3763234&CY=gb&LG=en&DB=EPD)
Lewis acid catalystsPatent US2478114 (http://l2.espacenet.com/dips/viewer?PN=US2478114&CY=gb&LG=en&DB=EPD)
hydrosulfite catalystPatent US1954433 (http://l2.espacenet.com/dips/viewer?PN=US1954433&CY=gb&LG=en&DB=EPD)
carboxylic acid, amine and xylene or amylbenzene distilledPatent US3288794 (http://l2.espacenet.com/dips/viewer?PN=US3288794&CY=gb&LG=en&DB=EPD)
dimethylamides using alkali metals/alkoxide catalystsPatent US4139557 (http://l2.espacenet.com/dips/viewer?PN=US4139557&CY=gb&LG=en&DB=EPD)
dimethylacetamide, MoO3 catalystPatent US1582675 (http://l2.espacenet.com/dips/viewer?PN=US1582675&CY=gb&LG=en&DB=EPD)
formamidePatent US2692882 (http://l2.espacenet.com/dips/viewer?PN=US2692882&CY=gb&LG=en&DB=EPD)
column 2 it says you can use Pd/C hydrogenation of an IAA amide at one atmosphere pressure. I found an example of atmospheric pressure hydrogenation here.http://www.orgsyn.org/orgsyn/prep.asp?prep=cv5p0586 (http://www.orgsyn.org/orgsyn/prep.asp?prep=cv5p0586)
Patent US5192770 (http://l2.espacenet.com/dips/viewer?PN=US5192770&CY=gb&LG=en&DB=EPD)
Post 397806 (missing)
(Aurelius: "US patent 1793176 Tryptamines through grignards", General Discourse)Post 270360 (https://www.thevespiary.org/talk/index.php?topic=12941.msg27036000#msg27036000)
(Lilienthal: "Re: Indole Grignards", Tryptamine Chemistry)Chemistry and Industry 1388-89 (1964) (https://www.thevespiary.org/rhodium/Rhodium/chemistry/dmt.indole.grignard.html)
(https://www.thevespiary.org/rhodium/Rhodium/chemistry/dmt.indole.grignard.html)(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_imgs/pdf.gif)
Post 482491 (https://www.thevespiary.org/talk/index.php?topic=12941.msg48249100#msg48249100)
(Rhodium: "Propynylindole and 3-Indolylacetone", Tryptamine Chemistry)J. Chem. Soc. 3172-3175 (1952) (https://www.thevespiary.org/rhodium/Rhodium/pdf/3-indolylacetone.pdf)
(https://www.thevespiary.org/rhodium/Rhodium/pdf/3-indolylacetone.pdf)If the corresponding n,n-dimethyltryptamine were the intended target, it could serve as a precursor for psilocin, methinks, via catalytic removal of the benzyl group to give psilocin, and subsequent esterification would be a good idea, due to the instability of 4-OH tryptamines.