ChemicalBook CAS DataBase List 5-Methoxytryptamine

5-Methoxytryptamine synthesis

12synthesis methods

Product Name:5-Methoxytryptamine
CAS Number:608-07-1
Molecular formula:C11H14N2O
Molecular Weight:190.24

5-Methoxytryptamine (358) was synthesized from 3-(2-iodoethyl)-5-methoxyindole (176) by reaction with 1-methyl-benzylamine (MeCN, 24 h, RT) and subsequent catalytic debenzylation of 44 (H2, Pd/C, EtOH, 24 h, RT, 4 bar). The resulting 5-methoxytryptamine (358 was then reacted with 4-bromobenzoylchloride (THF, NEt3, RT, ON) and the resulting tryptamide 359 was reduced with aluminum hydride to N-(4-bromobenzyl)-5-methoxytryptamine (19) (LiAlH4, AlCl3, Et2O, 5 h, RT), which was isolated as its hydrogen oxalate salt.
synthesis of 5-Methoxytryptamine

Ethyl 3-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-5-methoxy-1H-indole-2-carboxylate

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608-07-1
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Yield:608-07-1 99%

Reaction Conditions:

Stage #1: 2-carboxyethyl-3-(2-phthalimidoethyl)-5-methoxyindolewith lithium hydroxide monohydrate;sodium hydroxide at 88 - 90;
Stage #2: with hydrogenchloride in lithium hydroxide monohydrate at 10 - 110;Temperature;

Steps:

1.3; 9

Add 200 g of water and 40 g of sodium hydroxide to the reaction vessel, wait for the solution to dissolve at room temperature, add 248.5 g of compound II, warm to 88-90 ° C, and react for 5-6 hours; 10 ~ 20 ° C, slowly add 192.4g of concentrated hydrochloric acid (36wt%), after the addition is complete, raise the temperature to 107 ~ 110 ° C, and react for 1 ~ 2h; then reduce the reaction solution to room temperature, filter, and wash the filter cake with water until neutral It was dried at 55 ° C to obtain 119.3 g of pure compound III with a yield of 99.0%.

References:

CN110818610,2020,A Location in patent:Paragraph 0049; 0055; 0087-0089