3-(2-(Dimethylamino)ethyl)-1H-indol-4-yl acetate (4-AcO-DMT)

Page 1

Reaxys

PubChem

eMolecules

Reactions (13)

Yield

Substances (3)

Citations (5)

Conditions

References

1

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Rx-ID: 160611 Find similar reactions

With ethylene glycol dimethyl ether

2

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Troxler et al.

Helvetica Chimica Acta, 1959 , vol. 42, p. 2073,2098 Full Text Show Details

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Rx-ID: 5146799 Find similar reactions

With hydrogen; sodium acetate; palladium on activated charcoal in benzene

P=3102.89 Torr; 4 h;

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Nichols, David E.; Frescas, Stewart

Synthesis, 1999 , # 6 p. 935 - 938 Title/Abstract Full Text View citing articles Show Details

3

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Rx-ID: 5493846 Find similar reactions

Sandoz

Patent: US3078214 , 1963 ; Chem.Abstr., 1963 , vol. 59, # 8707a Full Text Show Details

Sandoz Ltd.

Patent: US3075992 , 1958 ; Chem.Abstr., 1964 , vol. 61, # 5613e Full Text Show Details

4

Synthesize Find similar Multi-step reaction with 4 steps 1: diethyl ether / 3 h / 5 - 10 °C 2: diethyl ether; CH2Cl2 / 6 h 3: 94.8 percent / LiAlH4 / tetrahydrofuran; dioxane / 1.) 4 h, 2.) reflux, 20 h 4: H2, AcONa / 10 percent Pd/C / benzene / 4 h / 3102.89 Torr View Scheme

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Rx-ID: 16302255 Find similar reactions

Nichols, David E.; Frescas, Stewart

Synthesis, 1999 , # 6 p. 935 - 938 Title/Abstract Full Text View citing articles Show Details


5

Synthesize Find similar Multi-step reaction with 2 steps 1: 94.8 percent / LiAlH4 / tetrahydrofuran; dioxane / 1.) 4 h, 2.) reflux, 20 h 2: H2, AcONa / 10 percent Pd/C / benzene / 4 h / 3102.89 Torr View Scheme

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Rx-ID: 16305511 Find similar reactions

Nichols, David E.; Frescas, Stewart

Synthesis, 1999 , # 6 p. 935 - 938 Title/Abstract Full Text View citing articles Show Details

6

Synthesize Find similar Multi-step reaction with 3 steps 1: diethyl ether; CH2Cl2 / 6 h 2: 94.8 percent / LiAlH4 / tetrahydrofuran; dioxane / 1.) 4 h, 2.) reflux, 20 h 3: H2, AcONa / 10 percent Pd/C / benzene / 4 h / 3102.89 Torr View Scheme

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Rx-ID: 16315307 Find similar reactions

Nichols, David E.; Frescas, Stewart

Synthesis, 1999 , # 6 p. 935 - 938 Title/Abstract Full Text View citing articles Show Details

7

Synthesize Find similar With lithium aluminium tetrahydride in tetrahydrofuran

Reflux; Hide Experimental Procedure

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Rx-ID: 37741614 Find similar reactions

Furman, Svetlana; Nissim-Bardugo, Elinor; Zeeli, Shani; Weitman, Michal; Nudelman, Abraham; Finkin-Groner, Efrat; Moradov, Dorit; Shifrin, Helena; Schorer-Apelbaum, Donna; Weinstock, Marta

Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 10 p. 2283 - 2287 Title/Abstract Full Text View citing articles Show Details


Synthesis of 3-(2-(dimethylamino)ethyl)-1H-indoles

General procedure: To a suspension of LiAlH4 (14.4 mmol) in anhydrous THF (45 mL) was added drop-wise a solution of an indolyl-oxoacetamide (4.1 mmol) in anhydrous THF (15 mL). The mixture was refluxed for 2-4 h, cooled to room temperature, and a solution of 15percent NaOH was added drop-wise to destroy the excess hydride, the mixture was filtered through celite, and the filtrate was evaporated to give the 3-(2-(dimethylamino)ethyl)-1H-indoles.

8

Synthesize Find similar Multi-step reaction with 2 steps 1: tetrahydrofuran / 4 h / 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / |Reflux View Scheme

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Rx-ID: 37741620 Find similar reactions

Furman, Svetlana; Nissim-Bardugo, Elinor; Zeeli, Shani; Weitman, Michal; Nudelman, Abraham; Finkin-Groner, Efrat; Moradov, Dorit; Shifrin, Helena; Schorer-Apelbaum, Donna; Weinstock, Marta

Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 10 p. 2283 - 2287 Title/Abstract Full Text View citing articles Show Details

9

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Rx-ID: 5145292 Find similar reactions

in methanol

0.166667 h; Yield given;

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Nichols, David E.; Frescas, Stewart

Synthesis, 1999 , # 6 p. 935 - 938 Title/Abstract Full Text View citing articles Show Details

10

Synthesize Find similar Multi-step reaction with 5 steps 1: diethyl ether / 3 h / 5 - 10 °C 2: diethyl ether; CH2Cl2 / 6 h

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Rx-ID: 16302257 Find similar reactions

Nichols, David E.; Frescas, Stewart

Synthesis, 1999 , # 6 p. 935 - 938 Title/Abstract Full Text View citing articles Show Details


3: 94.8 percent / LiAlH4 / tetrahydrofuran; dioxane / 1.) 4 h, 2.) reflux, 20 h 4: H2, AcONa / 10 percent Pd/C / benzene / 4 h / 3102.89 Torr 5: methanol / 0.17 h View Scheme

11

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Multi-step reaction with 2 steps 1: H2, AcONa / 10 percent Pd/C / benzene / 4 h / 3102.89 Torr 2: methanol / 0.17 h View Scheme

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Rx-ID: 16305176 Find similar reactions

Nichols, David E.; Frescas, Stewart

Synthesis, 1999 , # 6 p. 935 - 938 Title/Abstract Full Text View citing articles Show Details

12

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Multi-step reaction with 3 steps 1: 94.8 percent / LiAlH4 / tetrahydrofuran; dioxane / 1.) 4 h, 2.) reflux, 20 h 2: H2, AcONa / 10 percent Pd/C / benzene / 4 h / 3102.89 Torr 3: methanol / 0.17 h View Scheme

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Rx-ID: 16305513 Find similar reactions

Nichols, David E.; Frescas, Stewart

Synthesis, 1999 , # 6 p. 935 - 938 Title/Abstract Full Text View citing articles Show Details

13

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Synthesize

Rx-ID: 16315309


Find similar Multi-step reaction with 4 steps 1: diethyl ether; CH2Cl2 / 6 h 2: 94.8 percent / LiAlH4 / tetrahydrofuran; dioxane / 1.) 4 h, 2.) reflux, 20 h 3: H2, AcONa / 10 percent Pd/C / benzene / 4 h / 3102.89 Torr 4: methanol / 0.17 h View Scheme

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Nichols, David E.; Frescas, Stewart

Synthesis, 1999 , # 6 p. 935 - 938 Title/Abstract Full Text View citing articles Show Details


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