3-(diethylaminomethyl)-5-benzyloxyindol

Base Information

Chemical Name:3-(diethylaminomethyl)-5-benzyloxyindol
CAS No.:190182-62-8
Molecular Formula:C₂₀H₂₄N₂O
Molecular Weight:308.423
Hs Code.:

Synonyms:3-(diethylaminomethyl)-5-benzyloxyindol

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Chemical Property of 3-(diethylaminomethyl)-5-benzyloxyindol

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Technology Process of 3-(diethylaminomethyl)-5-benzyloxyindol

There total 1 articles about 3-(diethylaminomethyl)-5-benzyloxyindol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 1215-59-4
5-benzyloxy-1H-indole

: 109-89-7
diethylamine

: 190182-62-8
3-(diethylaminomethyl)-5-benzyloxyindol

Guidance literature:: With acetic acid; at 6 - 21 ℃; for 17.5h; Et₂NH in AcOH and 30 min after aq. CH₂O mixing at 6 deg C; pouring into a pre-cooled indole; quenching with 10 percent NaOH;
DOI:10.1111/j.2042-7158.1997.tb06789.x

Reference yield: 82.7%

: 190182-62-8
3-(diethylaminomethyl)-5-benzyloxyindol

: 74-88-4
methyl iodide

: 2436-15-9
NSC 73391

Guidance literature:: In tetrahydrofuran; water; MeI adding to a pre-cooled indole (5 deg C) in THF; stirring overnight; aq. KCN adding; stirring at reflux under Ar;
DOI:10.1111/j.2042-7158.1997.tb06789.x

Reference yield:

: 190182-62-8
3-(diethylaminomethyl)-5-benzyloxyindol

: methyl 3-amino-2-(5-(benzyloxy)-1H-indol-3-yl)propanoate hydrochloride

Guidance literature:: Multi-step reaction with 5 steps

1: 82.7 percent / tetrahydrofuran; H₂O / MeI adding to a pre-cooled indole (5 deg C) in THF; stirring overnight; aq. KCN adding; stirring at reflux under Ar

2: 77 percent / Na / 2.5 h / 90 - 105 °C / Na adding insmall portions to a soln. of the indole in (EtO)2CO at 90 deg C; stirring 2 h at 105 deg C; evapg.

3: 91 percent / H₂ / Raney-Ni W-2 / 8 h / 21 °C / 2585.74 Torr / in the excess of Ac₂O

4: 88 percent / aq. NaOH / 8 h / refluxing under Ar; diluting with H₂O; acidifying with AcOH up to pH 6.12; ppt. collecting by vacuum filtration

5: 77.6 percent / SOCl₂; HCl / methanol; dioxane / 18 h / -10 - 21 °C / SOCl₂ adding to a pre-cooled susp. of the acid in MeOH, stirring under Ar, evapg., treated with aq. K₂CO₃ and with 4 N HCl

With hydrogenchloride; sodium hydroxide; thionyl chloride; hydrogen; sodium; Raney-Ni W-2; In tetrahydrofuran; 1,4-dioxane; methanol; water; 1: Substitution / 2: Substitution / 3: Reduction / 4: Hydrolysis / 5: Esterification;
DOI:10.1111/j.2042-7158.1997.tb06789.x