2-(5-Methoxy-1H-indol-3-yl)ethan-1-amine (5-Methoxytryptamine) by Asch

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Reactions (57)

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Substances (7)

Citations (59)

Conditions

References

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Rx-ID: 82992 Find similar reactions

und Erwaermen des Reaktionsprodukts Natrium in Aethanol;

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Wieland et al.

Justus Liebigs Annalen der Chemie, 1934 , vol. 513, p. 1,18 Full Text Show Details

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Rx-ID: 82993 Find similar reactions

With diethyl ether

Erwaermen des Reaktionsprodukts mit Natrium und Aethanol;

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Wieland et al.

Justus Liebigs Annalen der Chemie, 1934 , vol. 513, p. 1,18 Full Text Show Details

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Rx-ID: 292564 Find similar reactions

Pietra

Farmaco, Edizione Scientifica, 1958 , vol. 13, p. 75,78 Full Text Show Details

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Rx-ID: 331041 Find similar reactions

Abramovitch; Shapiro

Journal of the Chemical Society, 1956 , p. 4589,4591 Full Text Show Details

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Rx-ID: 1799394 Find similar reactions

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99%

With palladium on activated charcoal; hydrogen in methanol

T=20°C;

Zhang, Pu Yong; Wan, Sheng Biao; Ren, Su Mei; Jiang, Tao

Chinese Chemical Letters, 2010 , vol. 21, # 11 p. 1307 - 1309 Title/Abstract Full Text View citing articles Show Details

With hydrogen; palladium on activated charcoal in ethanol

P=2585.7 Torr; 12 h;

Repke, David B.; Grotjahn, Douglas B.; Shulgin, Alexander T.

Journal of Medicinal Chemistry, 1985 , vol. 28, # 7 p. 892 - 896 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 5221968 Find similar reactions

99%

With sodium hydroxide in methanol

Hydrolysis; decarboxylation; 4 h; Heating;

Somei, Masanori; Fukui, Yoshikazu; Hasegawa, Masakazu; Oshikiri, Naoki; Hayashi, Toshikatsu

Heterocycles, 2000 , vol. 53, # 8 p. 1725 - 1736 Title/Abstract Full Text View citing articles Show Details

With water

Hydrolysis;

Somei, Masanori; Oshikiri, Naoki; Hasegawa, Masakazu; Yamada, Fumio

Heterocycles, 1999 , vol. 51, # 6 p. 1237 - 1242 Title/Abstract Full Text View citing articles Show Details

With sodium hydroxide

Heating;

Somei, Masanori; Iwaki, Takako; Yamada, Fumio; Tanaka, Yoshio; Shigenobu, Koki; Koike, Katsuo; Suzuki, Nobuo; Hattori, Atsuhiko

Heterocycles, 2006 , vol. 68, # 8 p. 1565 - 1569 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 5443106 Find similar reactions

Adlerova,E. et al.

Collection of Czechoslovak Chemical Communications, 1960 , vol. 25, p. 784 - 796 Full Text View citing articles Show Details

Flaugh; Crowell; Clemens; Sawyer

Journal of Medicinal Chemistry, 1979 , vol. 22, # 1 p. 63 - 69 Title/Abstract Full Text View citing articles Show Details

Kralt,T. et al.

Recueil des Travaux Chimiques des Pays-Bas, 1961 , vol. 80, p. 313 - 324 Full Text View citing articles Show Details

Julia; Manoury

Bulletin de la Societe Chimique de France, 1965 , p. 1411,1413 Full Text Show Details

Julia et al.

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1960 , vol. 251, p. 394 Full Text Show Details

Heinzelman; Szmuszkovicz

Progress in Drug Research, 1963 , vol. 6, p. 75,76-150

Chem.Abstr., 1964 , vol. 60, # 13215b Full Text Show Details

Buzas et al.

Synthesis, 1977 , p. 129 Full Text Show Details

Szmuszkovicz et al.

Journal of Organic Chemistry, 1960 , vol. 25, p. 857,858 Full Text Show Details

Bertaccini; Vitali

Farmaco, Edizione Scientifica, 1967 , vol. 22, p. 229,231 Full Text Show Details

Takatori; Takashima

Yakugaku Zasshi, 1963 , vol. 83, p. 795,798 Full Text Show Details

Grandberg et al.

Doklady Chemistry, 1967 , vol. 176, p. 828 Doklady Akademii Nauk SSSR, 1967 , vol. 176, p. 583 Full Text Show Details

Richter Gedeon Vegyeszeti Gyar R.T.

Patent: FR2261271DE2344919 , 1973 ; Chem.Abstr., vol. 80, # 146016 Full Text Show Details

Suvorov et al.

Chemistry of Heterocyclic Compounds (New York, NY, United States), 1974 , vol. 10, p. 1316,1320 Khimiya Geterotsiklicheskikh Soedinenii, 1974 , vol. 10, p. 1496 Full Text Show Details

Szantay et al.

Synthesis, 1974 , p. 354 Full Text Show Details

Grandberg; Bobrova

Chemistry of Heterocyclic Compounds (New York, NY, United States), 1973 , vol. 9, p. 196,199 Khimiya Geterotsiklicheskikh Soedinenii, 1973 , vol. 9, p. 213 Full Text Show Details

Mndzhoyan; Papayan

Izvestiya Akademii Nauk Armyanskoi SSR, Khimicheskie Nauki, 1961 , vol. 14, p. 603 Chem.Abstr., 1963 , vol. 58, # 4497c Full Text Show Details

Supniewski et al.

Dissertationes Pharmaceuticae, 1961 , vol. 13, p. 205,206-217 Chem.Abstr., 1962 , # 692 Full Text Show Details

Lab.francais de chimiotherapie

Patent: US2920080 , 1960 ; Chem.Abstr., 1960 , vol. 54, # 13019a Full Text Show Details

May and Baker Ltd.

Patent: GB841524 , 1956 ; Chem.Abstr., 1962 , vol. 56, # 1431 Full Text Show Details

Tacconi

Farmaco, Edizione Scientifica, 1965 , vol. 20, p. 891,895,899 Full Text View citing articles Show Details

Saito; Kikugawa

Journal of Heterocyclic Chemistry, 1979 , vol. 16, p. 1325,1327,1328 Full Text View citing articles Show Details

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Eli Lilly and Company

Patent: US5158956 A1, 1992 ; Title/Abstract Full Text Show Details

Illustrative examples of such compounds includes: 5-methoxytryptamine; 5-aminocarbonoyltryptamine; 5-methoxy-3-(1,2,3,6-tetrahydropyridine-4-yl)indole; N,N-di-n-propyl-5-carbamoyltryptamine; N,N-dimethyl-5-methoxytryptamine; N,N-diethyl-5-methoxytryptamine; N,N-di-n-propyl-5-methoxytryptamine; 5-methoxy-3-2-[1-(4-phenyl)-1,2,3,6-tetrahydropyridyl]ethyl]indole; N,N-dimethyl-5-hydroxytryptamine;

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Illustrative examples of such compounds includes:

Eli Lilly and Company

Patent: US5096908 A1, 1992 ; Title/Abstract Full Text Show Details

5-methoxytryptamine; 5-aminocarbonoyltryptamine; 5-methoxy-3-(1,2,3,6-tetrahydropyridine-4-yl)-indole; N,N-di-n-propyl-5-carbamoyltryptamine; N,N-dimethyl-5-methoxytryptamine; N,N-diethyl-5-methoxytryptamine; N,N-di-n-propyl-5-methoxytryptamine; 5-methoxy-3-[2-[1-(4-phenyl)-1,2,3,6-tetrahydropyridyl]ethyl]indole; N,N-dimethyl-5-hydroxytryptamine; ... Hide Details

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Title/Abstract Full Text Show Details

Preparing of 5-methoxytryptamine STR4

Preparing of 5-methoxytryptamine STR4 Into a 3-neck 3 liter flask, provided with stirrer, cooler and loading funnel, there are introduced 58.86 g (0.15 moles) of 2-carboxyethyl-3-2-phthalimidoethyl-5-methoxy-indole and 187.5 ml (15 g; 0.375 moles) of 2N NaOH and the mixture is refluxed at 135° C. for 2.5 hours, thereby providing a complete solution. By holding stirring and temperature, there are added, in 30 minutes, 750 ml of H2 SO4 (at 20percent) (v/v), by further reflux processing for 4 hours. At the end, the solution is cooled (for a night in a refrigerator or for 3 hours in an ice bath), by removing by filtration the precipitated phtalic acid. The solution is made alkaline by cooling with 30percent NaOH and extracted by CH2 Cl2 *3; the collected extracted materials are washed with water, dried on anhydrous Na2 SO4 and evaporated, thereby providing 20.25 g (yield 71percent) of crude 5-methoxytryptamine.

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Fraschini; Franco; Di Bella; Luigi; Duranti; Ermanno

Patent: US5122535 A1, 1992 ; Title/Abstract Full Text Show Details

Purifying of 5-methoxytryptamine STR5

Purifying of 5-methoxytryptamine STR5 To purify 5-methoxytriptamine, 19 g (0.1 moles) of 5-methoxytriptamine (in a raw condition) and 76 ml (58.86-0.36 moles) of hexamethyldisilazane are refluxed for a night in a flask with sodium hydroxide protected cooling. The solution is firstly distilled under normal pressure for recovering excess HMDS (43.6 g; 0.27 moles; m.p. 124°-5° C.) and then under a reduced pressure, thereby providing a mixture of biderivative (20.26 g; m.p 135°-40° C. at 0.1 Torr) and monoderivative material (5.25 g; m.p. 165° C. at 0.1 Torr). The silyl derivative is hydrolized by aqueous methanol, thereby providing 15.36 (0.08 moles) with a yield of 80percent. The mixture is crystalized from ethanol, so as to provide a white product having a m.p of 120°-1° C.

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Fraschini; Franco; Di Bella; Luigi; Duranti; Ermanno

Patent: US5122535 A1, 1992 ;

With zinc(II) chloride

T=180°C;

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Rx-ID: 5443107 Find similar reactions

Spaeth; Lederer

Chemische Berichte, 1930 , vol. 63, p. 2102,2106 Full Text View citing articles Show Details

Hoshino; Kobayashi

Justus Liebigs Annalen der Chemie, 1935 , vol. 516, p. 81,88 Justus Liebigs Annalen der Chemie, 1935 , vol. 520, p. 11,19 Full Text Show Details

Quadbeck; Roehm

Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1954 , vol. 297, p. 229,233 Full Text Show Details

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65%

With ammonia; sodium in tetrahydrofuran

T=-78°C; 0.25 h;

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Rx-ID: 8684110 Find similar reactions

Amat; Seffar; Llor; Bosch

Synthesis, 2001 , # 2 p. 267 - 275 Title/Abstract Full Text View citing articles Show Details

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66%

With sodium in tetrahydrofuran; ammonia

T=-33°C; 1.5 h;

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Rx-ID: 9007347 Find similar reactions

Revial, Gilbert; Jabin, Ivan; Lim, Sethy; Pfau, Michel

Journal of Organic Chemistry, 2002 , vol. 67, # 7 p. 2252 - 2256 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 9199639 Find similar reactions

With lithium aluminium tetrahydride in tetrahydrofuran

8 h; Heating;

Wu, Tom Y. H.; Schulte, Peter G.

Organic Letters, 2002 , vol. 4, # 23 p. 4033 - 4035 Title/Abstract Full Text View citing articles Show Details

With lithium aluminium tetrahydride in tetrahydrofuran

18 h; Reflux; Hide Experimental Procedure

Blough, Bruce E.; Landavazo, Antonio; Partilla, John S.; Decker, Ann M.; Page, Kevin M.; Baumann, Michael H.; Rothman, Richard B.

Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 19 p. 4754 - 4758 Title/Abstract Full Text View citing articles Show Details

General procedure: To a solution of 4’-Fluoro-2,3-di-oxotryptamine (3b, 644 mg, 3.12 mmol) in THF (30 mL), a 1.0 M LiAlH4/THF solution (16 mL, 16 mmol) was added slowly and the mixture was refluxed for 18 h. The reaction was quenched with water/THF (1/1) and made basic (pH 10) with 3 N aqueous NaOH. The solids were filtered through Celite; the filtrate was dried with anhydrous MgSO4and concentrated. The crude material was purified by automated flash chromatography (silica gel, 20percent MeOH/DCM) to obtain 130 mg of colorless oil (23percent). This material was dissolved in diethyl ether (100 mL) and MeOH (1 mL) and a solution of Fumaric Acid (90 mg, 0.77 mmol) in MeOH (9 mL) was added. The reaction stirred at room temperature for 60 h and the resulting solids were filtered, washed with ether and dried. The dry solids were recrystallized (MeOH/ethyl acetate) to yield 70.3 mg of product

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With sulfuric acid

0.166667 h; Heatingmicrowave irradiation;

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Rx-ID: 9323751 Find similar reactions

He, Ling; Li, Ju-Lian; Zhang, Jian-Jun; Su, Pu; Zheng, Shi-Long

Synthetic Communications, 2003 , vol. 33, # 5 p. 741 - 747 Title/Abstract Full Text View citing articles Show Details

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84%

With potassium hydroxide in methanol

9 h; Heating;

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Rx-ID: 9424346 Find similar reactions

Thomson, Douglas W.; Commeureuc, Aurelien G. J.; Berlin, Stefan; Murphy, John A.

Synthetic Communications, 2003 , vol. 33, # 20 p. 3631 - 3641 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 9870819 Find similar reactions

73%

With lithium aluminium tetrahydride in tetrahydrofuran

T=0 - 20°C; 40 h;

Nelson, Hosea M.; Reisberg, Solomon H.; Shunatona, Hunter P.; Patel, Jigar S.; Toste, F. Dean

Angewandte Chemie - International Edition, 2014 , vol. 53, # 22 p. 5600 - 5603 Angew. Chem., 2014 , vol. 126, # 22 p. 5706 - 5709,4 Title/Abstract Full Text View citing articles Show Details

With lithium aluminium tetrahydride in

Gurkan, A. Selen; Karabay, Arzu; Buyukbingol, Zeliha; Adejare, Adeboye; Buyukbingol, Erdem

tetrahydrofuran

Heating;

Archiv der Pharmazie, 2005 , vol. 338, # 2-3 p. 67 - 73 Title/Abstract Full Text View citing articles Show Details

Ates-Alagoz; Buyukbingol; Buyukbingol, Erdem

Pharmazie, 2005 , vol. 60, # 9 p. 643 - 647 Title/Abstract Full Text View citing articles Show Details

Stage #1: With lithium aluminium tetrahydride in tetrahydrofuran

T=20°C; Inert atmosphere; Stage #2: With water in tetrahydrofuran

LES LABORATOIRES SERVIER

Patent: US2010/204276 A1, 2010 ; Location in patent: Page/Page column 3 ;

T=0°C; Hide Experimental Procedure

Title/Abstract Full Text Show Details

1.B:

Under argon, add dropwise a solution of 4.48 g of the compound obtained in Step A in 100 ml of tetrahydrofuran to a solution of 7.80 g of lithium aluminium hydride in 100 ml of tetrahydrofuran. Stir at ambient temperature for 20 hours. Cool to 0° C. and hydrolyse with water. Filter the reaction mixture over Celite and extract with ethyl acetate. Dry the organic phase over sodium sulfate, filter and evaporate. The compound obtained is isolated in the form of a brown solid. Melting point: 101-102° C. Hide Details

Multi-step reaction with 2 steps 1: sodium tetrahydroborate / tetrahydrofuran; methanol / 20 °C 2: palladium on activated charcoal; hydrogen / methanol / 20 °C View Scheme

Zhang, Pu Yong; Wan, Sheng Biao; Ren, Su Mei; Jiang, Tao

Chinese Chemical Letters, 2010 , vol. 21, # 11 p. 1307 - 1309 Title/Abstract Full Text View citing articles Show Details

With lithium aluminium tetrahydride in tetrahydrofuran

T=20°C;

Cuny, Gregory D.; Ulyanova, Natalia P.; Patnaik, Debasis; Liu, Ji-Feng; Lin, Xiangjie; Auerbach, Ken; Ray, Soumya S.; Xian, Jun; Glicksman, Marcie A.; Stein, Ross L.; Higgins, Jonathan M.G.

Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 5 p. 2015 - 2019 Title/Abstract Full Text View citing articles Show Details

With lithium aluminium tetrahydride in tetrahydrofuran

Reflux;

Nirogi, Ramakrishna V.S.; Kambhampati, Ramasastri; Kothmirkar, Prabhakar; Konda, Jagadishbabu; Bandyala, Thrinath Reddy; Gudla, Parandhama; Arepalli, Sobhanadri; Gangadasari, Narasimhareddy P.; Shinde, Anil K.; Deshpande, Amol D.; Dwarampudi, Adireddy; Chindhe, Anil K.; Dubey, Pramod Kumar

Journal of Enzyme Inhibition and Medicinal Chemistry, 2012 , vol. 27, # 3 p. 443 - 450 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 10292317 Find similar reactions

89%

With ammonium bromide; ethylenediamine

T=100°C; 7 h; Microwave irradiation;

Bartolucci, Silvia; Mari, Michele; Bedini, Annalida; Piersanti, Giovanni; Spadoni, Gilberto

Journal of Organic Chemistry, 2015 , vol. 80, # 6 p. 3217 - 3222 Title/Abstract Full Text View citing articles Show Details

69.7%

With sulfuric acid in water

8 h; Heating;

Venkatachalam; Salaskar; Chattopadhyay; Barik; Mishra; Gangabhagirathi; Priyadarsini

Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 18 p. 6414 - 6419 Title/Abstract Full Text View citing articles Show Details

With sodium hydroxide in 2-methylpropan-1-ol

Nestec S. A.

Patent: US4506080 A1, 1985 ;

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Title/Abstract Full Text Show Details

4:Preparation of mexamine

EXAMPLE 4 Preparation of mexamine The melatonine obtained in Example 3 was taken up in 300 g isobutanol. To this mixture were added 30 g sodium hydroxide and 3 g of sodium dithionite and the whole mixture was refluxed at 105° C. for 2 hours under nitrogen. The reaction mixture was then cooled and extracted with 500 g water. The aqueous phase which contained sodium acetate formed as well as excess sodium hydroxide, was separated. The isobutanol phase was acidified to pH 2 with 32percent hydrochloric acid and then concentrated which induced the crystallisation of the mexamine which was then filtered. 36 g of crude mexamine was thus obtained. After recrystallisation in 96percent ethanol, 30 g of white crystals of mexamine were obtained having a purity of 98.5percent. Hide Details

With sulfuric acid in water

T=80°C; 8 h; Hide Experimental Procedure

HERCULES TECHNOLOGY MANAGEMENT CO V, INC.; BLAGG, Julian

Patent: WO2011/47156 A1, 2011 ; Location in patent: Page/Page column 40 ; Title/Abstract Full Text Show Details

Preparation of Intermediate G A solution of Intermediate F (1.4 g, 6.03 mmol) in a 10percent NaOH solution (13.5 mL) was stirred at 80 °C for 8 hours. The reaction mixture was basified with 20percent NaOH (pH~10) and extracted with ethyl acetate (2 χ 50 mL). The combined ethyl acetate layers were washed with water (30 mL) and brine (20 mL), dried over anhydrous Na2S04, and the solvent was removed to afford the crude product, which was washed with pet ether (2 χ 10 ml) and n-pentane (10 mL) then dried to afford Intermediate G (1.2 g, crude), as pale brown solid. NMR (CDC13): δ 10.58 (bs, 1H), 7.20 (t, J= 8.78 Hz; 1H), 7.07 (s, 1H), 6.98 (s, 1H), 6.71-6.68 (m, III), 3.75 (s, 3U), 2.81-2.69 (m, 4H), 1.39 (bs, 2H).

With potassium hydoxide in ethanol

Zlotos, Darius P.; Riad, Noura M.; Osman, Mai B.; Dodda, Bala R.; Witt-Enderby, Paula A.

MedChemComm, 2015 , vol. 6, # 7 p. 1340 - 1344 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 5 steps 1: 100 percent / Et3N 2: Et3SiH / trifluoroacetic acid 3: 63 percent / Na2WO4*2H2O; aq. H2O2 / methanol; H2O 4: 85 percent / BF3

5: NaOH / Heating View Scheme

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Rx-ID: 12181918 Find similar reactions

Somei, Masanori; Iwaki, Takako; Yamada, Fumio; Tanaka, Yoshio; Shigenobu, Koki; Koike, Katsuo; Suzuki, Nobuo; Hattori, Atsuhiko

Heterocycles, 2006 , vol. 68, # 8 p. 1565 - 1569 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 12186593 Find similar reactions

Multi-step reaction with 4 steps 1: Et3SiH / trifluoroacetic acid 2: 63 percent / Na2WO4*2H2O; aq. H2O2 / methanol; H2O 3: 85 percent / BF3

4: NaOH / Heating View Scheme

Somei, Masanori; Iwaki, Takako; Yamada, Fumio; Tanaka, Yoshio; Shigenobu, Koki; Koike, Katsuo; Suzuki, Nobuo; Hattori, Atsuhiko

Heterocycles, 2006 , vol. 68, # 8 p. 1565 - 1569 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 4 steps 1: 97 percent / Et3SiH / trifluoroacetic acid / 3 h / 60 °C 2: 65 percent / H2O2 / Na2WO4*2H2O / methanol; H2O / 0.5 h / 20 °C 3: 94 percent / BF3 / 0.67 h / Heating 4: 99 percent / aq. NaOH / methanol / 4 h / Heating View Scheme

Somei, Masanori; Fukui, Yoshikazu; Hasegawa, Masakazu; Oshikiri, Naoki; Hayashi, Toshikatsu

Heterocycles, 2000 , vol. 53, # 8 p. 1725 - 1736 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 12197118 Find similar reactions

Multi-step reaction with 3 steps 1: 63 percent / Na2WO4*2H2O; aq. H2O2 / methanol; H2O 2: 85 percent / BF3

3: NaOH / Heating View Scheme

Somei, Masanori; Iwaki, Takako; Yamada, Fumio; Tanaka, Yoshio; Shigenobu, Koki; Koike, Katsuo; Suzuki, Nobuo; Hattori, Atsuhiko

Heterocycles, 2006 , vol. 68, # 8 p. 1565 - 1569 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 3 steps 1: 65 percent / H2O2 / Na2WO4*2H2O / methanol; H2O / 0.5 h / 20 °C 2: 94 percent / BF3 / 0.67 h / Heating 3: 99 percent / aq. NaOH / methanol / 4 h / Heating View Scheme

Somei, Masanori; Fukui, Yoshikazu; Hasegawa, Masakazu; Oshikiri, Naoki; Hayashi, Toshikatsu

Heterocycles, 2000 , vol. 53, # 8 p. 1725 - 1736 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 12197127 Find similar reactions

Multi-step reaction with 2 steps 1: 85 percent / BF3

2: NaOH / Heating View Scheme

Somei, Masanori; Iwaki, Takako; Yamada, Fumio; Tanaka, Yoshio; Shigenobu, Koki; Koike, Katsuo; Suzuki, Nobuo; Hattori, Atsuhiko

Heterocycles, 2006 , vol. 68, # 8 p. 1565 - 1569 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: 94 percent / BF3 / 0.67 h / Heating 2: 99 percent / aq. NaOH / methanol / 4 h / Heating View Scheme

Somei, Masanori; Fukui, Yoshikazu; Hasegawa, Masakazu; Oshikiri, Naoki; Hayashi, Toshikatsu

Heterocycles, 2000 , vol. 53, # 8 p. 1725 - 1736 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: 85 percent / BF3*MeOH / 0.17 h / Heating 2: H2O View Scheme

Somei, Masanori; Oshikiri, Naoki; Hasegawa, Masakazu; Yamada, Fumio

Heterocycles, 1999 , vol. 51, # 6 p. 1237 - 1242 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 13166733 Find similar reactions

Multi-step reaction with 3 steps 1: POCl3 / 0 °C 2: NH4OAc / 70 °C 3: LiAlH4 / tetrahydrofuran / Heating View Scheme

Gurkan, A. Selen; Karabay, Arzu; Buyukbingol, Zeliha; Adejare, Adeboye; Buyukbingol, Erdem

Archiv der Pharmazie, 2005 , vol. 338, # 2-3 p. 67 - 73 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 3 steps 1: diethyl ether / 6 h / Heating 2: NH3 / dioxane / 8 h / 20 °C 3: lithium aluminum hydride / tetrahydrofuran / 8 h / Heating View Scheme

Wu, Tom Y. H.; Schulte, Peter G.

Organic Letters, 2002 , vol. 4, # 23 p. 4033 - 4035 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 5 steps 1.1: BuLi / tetrahydrofuran; hexane / 0.25 h / -10 °C 1.2: tetrahydrofuran; hexane / 3 h / 0 °C 2.1: 5.4 g / NBS / tetrahydrofuran; hexane / 3 h / -78 °C 3.1: t-BuLi / pentane; diethyl ether / 0.17 h / -78 °C 3.2: CuBr*SMe2 / pentane; diethyl ether / 0.25 h / -78 °C 3.3: 50 percent / BF3*Et2O / pentane; diethyl ether / 4 h / -78 °C 4.1: 89 percent / Bu4NF / tetrahydrofuran / 0.17 h / 20 °C 5.1: 65 percent / NH3; Na / tetrahydrofuran / 0.25 h / -78 °C View Scheme

Amat; Seffar; Llor; Bosch

Synthesis, 2001 , # 2 p. 267 - 275 Title/Abstract Full Text View citing articles Show Details

Hide Details

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Multi-step reaction with 2 steps 1: 85 percent / tert-butylcatechol / xylene / 3 h / Heating 2: H2 / 10 percent Pd/C / ethanol / 12 h / 2585.7 Torr View Scheme

Repke, David B.; Grotjahn, Douglas B.; Shulgin, Alexander T.

Journal of Medicinal Chemistry, 1985 , vol. 28, # 7 p. 892 - 896 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 4 steps 1: sodium hydroxide; trichlorophosphate 2: ammonium acetate / benzene / Reflux 3: sodium tetrahydroborate / tetrahydrofuran; methanol / 20 °C 4: palladium on activated charcoal; hydrogen / methanol / 20 °C View Scheme

Zhang, Pu Yong; Wan, Sheng Biao; Ren, Su Mei; Jiang, Tao

Chinese Chemical Letters, 2010 , vol. 21, # 11 p. 1307 - 1309 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 3 steps 1.1: trichlorophosphate / 1.25 h / 0 - 38 °C 1.2: 0.08 h / 170 °C 2.1: ammonium acetate / 1.5 h / |Reflux 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 40 h / 0 - 20 °C View Scheme

Nelson, Hosea M.; Reisberg, Solomon H.; Shunatona, Hunter P.; Patel, Jigar S.; Toste, F. Dean

Angewandte Chemie - International Edition, 2014 , vol. 53, # 22 p. 5600 - 5603 Angew. Chem., 2014 , vol. 126, # 22 p. 5706 - 5709,4 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 3 steps 1: diethyl ether / 18 h / 40 °C 2: ammonia / 1,4-dioxane / 20 °C 3: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / |Reflux View Scheme

Blough, Bruce E.; Landavazo, Antonio; Partilla, John S.; Decker, Ann M.; Page, Kevin M.; Baumann, Michael H.; Rothman, Richard B.

Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 19 p. 4754 - 4758 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 13167712 Find similar reactions

Multi-step reaction with 2 steps 1: NH4OAc / 70 °C 2: LiAlH4 / tetrahydrofuran / Heating View Scheme

Gurkan, A. Selen; Karabay, Arzu; Buyukbingol, Zeliha; Adejare, Adeboye; Buyukbingol, Erdem

Archiv der Pharmazie, 2005 , vol. 338, # 2-3 p. 67 - 73 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 3 steps 1: ammonium acetate / benzene / Reflux 2: sodium tetrahydroborate / tetrahydrofuran; methanol / 20 °C 3: palladium on activated charcoal; hydrogen / methanol / 20 °C View Scheme

Zhang, Pu Yong; Wan, Sheng Biao; Ren, Su Mei; Jiang, Tao

Chinese Chemical Letters, 2010 , vol. 21, # 11 p. 1307 - 1309 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: piperidine; acetic acid / benzene / Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / Reflux View Scheme

Journal of Enzyme Inhibition and Medicinal Chemistry, 2012 , vol. 27, # 3 p. 443 - 450 Title/Abstract Full Text View citing articles Show Details

Hide Details

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Multi-step reaction with 2 steps 1: ammonium acetate / 1.5 h / |Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 40 h / 0 - 20 °C View Scheme

Nelson, Hosea M.; Reisberg, Solomon H.; Shunatona, Hunter P.; Patel, Jigar S.; Toste, F. Dean

Angewandte Chemie - International Edition, 2014 , vol. 53, # 22 p. 5600 - 5603 Angew. Chem., 2014 , vol. 126, # 22 p. 5706 - 5709,4 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 5 steps 1.1: 96 percent / 4-dimethylaminopyridine; pyridine / 14 h / 20 °C 2.1: 82 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 3.1: tristrimethylsilylsilane; azoisobutyronitrile / toluene / 12 h / Heating 3.2: 74 percent / p-toluenesulfonic acid / toluene / 2 h / Heating 4.1: 85 percent / hydrazine monohydrate / ethanol / 3 h / Heating 5.1: 84 percent / KOH / methanol / 9 h / Heating View Scheme

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Rx-ID: 14095539 Find similar reactions

Thomson, Douglas W.; Commeureuc, Aurelien G. J.; Berlin, Stefan; Murphy, John A.

Synthetic Communications, 2003 , vol. 33, # 20 p. 3631 - 3641 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 4 steps 1.1: 82 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: tristrimethylsilylsilane; azoisobutyronitrile / toluene / 12 h / Heating 2.2: 74 percent / p-toluenesulfonic acid / toluene / 2 h / Heating 3.1: 85 percent / hydrazine monohydrate / ethanol / 3 h / Heating 4.1: 84 percent / KOH / methanol / 9 h / Heating View Scheme

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Rx-ID: 14098441 Find similar reactions

Thomson, Douglas W.; Commeureuc, Aurelien G. J.; Berlin, Stefan; Murphy, John A.

Synthetic Communications, 2003 , vol. 33, # 20 p. 3631 - 3641 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: 85 percent / hydrazine monohydrate / ethanol / 3 h / Heating 2: 84 percent / KOH / methanol / 9 h / Heating View Scheme

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Rx-ID: 14108105 Find similar reactions

Thomson, Douglas W.; Commeureuc, Aurelien G. J.; Berlin, Stefan; Murphy, John A.

Synthetic Communications, 2003 , vol. 33, # 20 p. 3631 - 3641 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1.1: tristrimethylsilylsilane; azoisobutyronitrile / toluene / 12 h / Heating 1.2: 74 percent / p-toluenesulfonic acid / toluene / 2 h / Heating 2.1: 85 percent / hydrazine monohydrate / ethanol / 3 h / Heating 3.1: 84 percent / KOH / methanol / 9 h / Heating View Scheme

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Rx-ID: 14109813 Find similar reactions

Thomson, Douglas W.; Commeureuc, Aurelien G. J.; Berlin, Stefan; Murphy, John A.

Synthetic Communications, 2003 , vol. 33, # 20 p. 3631 - 3641 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: 10 percent aq. NaOH / 0.08 h / Heating; microwave irradiation

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Rx-ID: 14262096 Find similar reactions

He, Ling; Li, Ju-Lian; Zhang, Jian-Jun; Su, Pu; Zheng, Shi-Long

Synthetic Communications, 2003 , vol. 33, # 5 p. 741 - 747 Title/Abstract Full Text View citing articles Show Details

57 g

2: 20 percent H2SO4 / 0.17 h / Heating; microwave irradiation View Scheme

With potassium hydroxide

3 h; Reflux;

Prabhakar; Kumar, N. Vasanth; Reddy, M. Ravikanth; Sarma; Reddy, G. Om

Organic Process Research and Development, 1999 , vol. 3, # 3 p. 155 - 160 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 14516071 Find similar reactions

Multi-step reaction with 2 steps 1: NH3 / dioxane / 8 h / 20 °C 2: lithium aluminum hydride / tetrahydrofuran / 8 h / Heating View Scheme

Wu, Tom Y. H.; Schulte, Peter G.

Organic Letters, 2002 , vol. 4, # 23 p. 4033 - 4035 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: ammonia / 1,4-dioxane / 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / |Reflux View Scheme

Blough, Bruce E.; Landavazo, Antonio; Partilla, John S.; Decker, Ann M.; Page, Kevin M.; Baumann, Michael H.; Rothman, Richard B.

Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 19 p. 4754 - 4758 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: 60.5 percent / LiAlH4 / diethyl ether / 48 h / Heating 2: 66 percent / Na / tetrahydrofuran; liquid ammonia / 1.5 h / -33 °C View Scheme

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Rx-ID: 14962335 Find similar reactions

Revial, Gilbert; Jabin, Ivan; Lim, Sethy; Pfau, Michel

Journal of Organic Chemistry, 2002 , vol. 67, # 7 p. 2252 - 2256 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1: 83 percent / NH3 / methanol / 192 h / 20 °C 2: 60.5 percent / LiAlH4 / diethyl ether / 48 h / Heating 3: 66 percent / Na / tetrahydrofuran; liquid ammonia / 1.5 h / -33 °C View Scheme

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Rx-ID: 14985547 Find similar reactions

Revial, Gilbert; Jabin, Ivan; Lim, Sethy; Pfau, Michel

Journal of Organic Chemistry, 2002 , vol. 67, # 7 p. 2252 - 2256 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 4 steps 1.1: 5.4 g / NBS / tetrahydrofuran; hexane / 3 h / -78 °C 2.1: t-BuLi / pentane; diethyl ether / 0.17 h / -78 °C 2.2: CuBr*SMe2 / pentane; diethyl ether / 0.25 h / -78 °C 2.3: 50 percent / BF3*Et2O / pentane; diethyl ether / 4 h / -78 °C 3.1: 89 percent / Bu4NF / tetrahydrofuran / 0.17 h / 20 °C 4.1: 65 percent / NH3; Na / tetrahydrofuran / 0.25 h / -78 °C View Scheme

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Rx-ID: 15556604 Find similar reactions

Amat; Seffar; Llor; Bosch

Synthesis, 2001 , # 2 p. 267 - 275 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1.1: t-BuLi / pentane; diethyl ether / 0.17 h / -78 °C 1.2: CuBr*SMe2 / pentane; diethyl ether / 0.25 h / -78 °C 1.3: 50 percent / BF3*Et2O / pentane; diethyl ether / 4 h / -78 °C 2.1: 89 percent / Bu4NF / tetrahydrofuran / 0.17 h / 20 °C 3.1: 65 percent / NH3; Na / tetrahydrofuran / 0.25 h / -78 °C View Scheme

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Rx-ID: 15562173 Find similar reactions

Amat; Seffar; Llor; Bosch

Synthesis, 2001 , # 2 p. 267 - 275 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: 89 percent / Bu4NF / tetrahydrofuran / 0.17 h / 20 °C 2: 65 percent / NH3; Na / tetrahydrofuran / 0.25 h / -78 °C View Scheme

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Rx-ID: 15574321 Find similar reactions

Amat; Seffar; Llor; Bosch

Synthesis, 2001 , # 2 p. 267 - 275 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 4 steps 1: triethylamine; dioxane / anschliessend mit wss. HCl behandeln 2: palladium/charcoal; acetic acid / Hydrogenation 3: quinoline 4: sodium; isobutyl alcohol View Scheme

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Rx-ID: 22172123 Find similar reactions

Pietra

Farmaco, Edizione Scientifica, 1958 , vol. 13, p. 75,78 Full Text Show Details

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Multi-step reaction with 2 steps 1: aq.-ethanolic KOH 2: aqueous HCl View Scheme

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Rx-ID: 22187025 Find similar reactions

Abramovitch; Shapiro

Journal of the Chemical Society, 1956 , p. 4589,4591 Full Text Show Details

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Multi-step reaction with 5 steps 1: water; sulfuric acid 2: triethylamine; dioxane / anschliessend mit wss. HCl behandeln 3: palladium/charcoal; acetic acid / Hydrogenation 4: quinoline 5: sodium; isobutyl alcohol View Scheme

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Rx-ID: 22187577 Find similar reactions

Pietra

Farmaco, Edizione Scientifica, 1958 , vol. 13, p. 75,78 Full Text Show Details

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Multi-step reaction with 3 steps 1: palladium/charcoal; acetic acid / Hydrogenation 2: quinoline 3: sodium; isobutyl alcohol View Scheme

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Rx-ID: 22189944 Find similar reactions

Pietra

Farmaco, Edizione Scientifica, 1958 , vol. 13, p. 75,78 Full Text Show Details

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Multi-step reaction with 2 steps 1: quinoline 2: sodium; isobutyl alcohol View Scheme

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Rx-ID: 22190913 Find similar reactions

Pietra

Farmaco, Edizione Scientifica, 1958 , vol. 13, p. 75,78 Full Text Show Details

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in acetone

Hide Experimental Procedure

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Rx-ID: 24355519 Find similar reactions

Cemaf; Laboratories Besins Iscovesco

Patent: US6048868 A1, 2000 ; Title/Abstract Full Text Show Details

EXAMPLE 63 STR64 MDHCARBO2: 1-(6-methoxy-1,1-dimethyl-2,3,4,9-tetrahydro-1-β-carbolin-2-yl)-1-ethanone

EXAMPLE 63 STR64 MDHCARBO2: 1-(6-methoxy-1,1-dimethyl-2,3,4,9-tetrahydro-1-β-carbolin-2-yl)-1-ethanone Preparation: STR65 5-Methoxytryptamine 1 (1.14 g, 6 mmol) dissolved in acetone (50 mL) is stirred for one hour at room temperature. After evaporation of the acetone, the Schiff base II is obtained quantitatively.

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Multi-step reaction with 3 steps 1: iodine; 1H-imidazole; triphenylphosphine 2: sodium azide / N,N-dimethyl-formamide 3: 10 Pd/C; hydrogen / methanol / 760.05

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Rx-ID: 34055139 Find similar reactions

Gore, Sangram; Baskaran, Sundarababu; König, Burkhard

Organic Letters, 2012 , vol. 14, # 17 p. 4568 - 4571 Title/Abstract Full Text View citing articles Show Details

Torr View Scheme

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Multi-step reaction with 2 steps 1: sodium azide / N,N-dimethyl-formamide 2: 10 Pd/C; hydrogen / methanol / 760.05 Torr View Scheme

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Rx-ID: 34055143 Find similar reactions

Gore, Sangram; Baskaran, Sundarababu; König, Burkhard

Organic Letters, 2012 , vol. 14, # 17 p. 4568 - 4571 Title/Abstract Full Text View citing articles Show Details

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With 10 Pd/C; hydrogen in methanol

P=760.051 Torr;

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Rx-ID: 34055144 Find similar reactions

Gore, Sangram; Baskaran, Sundarababu; König, Burkhard

Organic Letters, 2012 , vol. 14, # 17 p. 4568 - 4571 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 4 steps 1: L-(+)-tartaric acid-urea melt / 70 °C 2: iodine; 1H-imidazole; triphenylphosphine 3: sodium azide / N,N-dimethyl-formamide 4: 10 Pd/C; hydrogen / methanol / 760.05 Torr View Scheme

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Rx-ID: 34055198 Find similar reactions

Gore, Sangram; Baskaran, Sundarababu; König, Burkhard

Organic Letters, 2012 , vol. 14, # 17 p. 4568 - 4571 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 5 h / 0 - 26 °C 2: potassium carbonate / methanol / 2 h / 26 °C 3: sodium hydroxide / water / 2.25 h / 26 °C 4: sulfuric acid / water / 8 h / 80 °C View Scheme

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Rx-ID: 34845874 Find similar reactions

HERCULES TECHNOLOGY MANAGEMENT CO V, INC.; BLAGG, Julian

Patent: WO2011/47156 A1, 2011 ; Title/Abstract Full Text Show Details

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Multi-step reaction with 2 steps 1: sodium hydroxide / water / 2.25 h / 26 °C 2: sulfuric acid / water / 8 h / 80 °C View Scheme

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Rx-ID: 34845955 Find similar reactions

HERCULES TECHNOLOGY MANAGEMENT CO V, INC.; BLAGG, Julian

Patent: WO2011/47156 A1, 2011 ; Title/Abstract Full Text Show Details

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Multi-step reaction with 3 steps 1: potassium carbonate / methanol / 2 h / 26 °C

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Rx-ID: 34846004 Find similar reactions

HERCULES TECHNOLOGY MANAGEMENT CO V, INC.; BLAGG, Julian

Patent: WO2011/47156 A1, 2011 ;

2: sodium hydroxide / water / 2.25 h / 26 °C 3: sulfuric acid / water / 8 h / 80 °C View Scheme

Title/Abstract Full Text Show Details

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91%

With sodium hydroxide

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Rx-ID: 3595114 Find similar reactions

Gynther, Jukka; Peura, Pekka; Salmi, Seija

Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1985 , vol. 39, # 10 p. 849 - 860 Title/Abstract Full Text Show Details

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Rx-ID: 5830861 Find similar reactions

5-Methoxyindol-3-(2-<2H2>)-acetamid, LiAl(2H)4;

Beck; Bosin

Biomedical Mass Spectrometry, 1979 , vol. 6, p. 19,20 Full Text Show Details

Amid (5), LiAlD4;

Shaw; Wright; Milne

Biomedical mass spectrometry, 1977 , vol. 4, # 6 p. 348 - 353 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 4 steps

Synthesize Find similar Gynther, Jukka; Peura, Pekka; Salmi, Seija

Rx-ID: 19064273 Find similar reactions

1: 88 percent / diethyl ether / 0.25 h / Ambient temperature 2: 96 percent / ammonia (gas) / toluene 3: 34 percent / lithium aluminium deuteride / tetrahydrofuran / 10 h / Heating 4: 91 percent / 0.1 M sodium hydroxide (aq.) View Scheme

Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1985 , vol. 39, # 10 p. 849 - 860 Title/Abstract Full Text Show Details

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Multi-step reaction with 3 steps 1: 96 percent / ammonia (gas) / toluene 2: 34 percent / lithium aluminium deuteride / tetrahydrofuran / 10 h / Heating 3: 91 percent / 0.1 M sodium hydroxide (aq.) View Scheme

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Rx-ID: 19069389 Find similar reactions

Gynther, Jukka; Peura, Pekka; Salmi, Seija

Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1985 , vol. 39, # 10 p. 849 - 860 Title/Abstract Full Text Show Details

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Multi-step reaction with 2 steps 1: 34 percent / lithium aluminium deuteride / tetrahydrofuran / 10 h / Heating 2: 91 percent / 0.1 M sodium hydroxide (aq.) View Scheme

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Rx-ID: 19080976 Find similar reactions

Gynther, Jukka; Peura, Pekka; Salmi, Seija

Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1985 , vol. 39, # 10 p. 849 - 860 Title/Abstract Full Text Show Details

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72%

With hydrogenchloride

2 h; Heating;

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Rx-ID: 4076224 Find similar reactions

Guengoer, Timur; Malabre, Patrice; Teulon, Jean-Marie; Camborde, Francoise; Meignen, Joelle; et al.

Journal of Medicinal Chemistry, 1994 , vol. 37, # 25 p. 4307 - 4316 Title/Abstract Full Text Show Details

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Multi-step reaction with 2 steps 1: 100 percent / KOH / ethanol / 6 h / Heating 2: 72 percent / 10percent aq. HCl / 2 h / Heating View Scheme

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Rx-ID: 18099075 Find similar reactions

Guengoer, Timur; Malabre, Patrice; Teulon, Jean-Marie; Camborde, Francoise; Meignen, Joelle; et al.

Journal of Medicinal Chemistry, 1994 , vol. 37, # 25 p. 4307 - 4316 Title/Abstract Full Text Show Details

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34%

With lithium aluminium deuteride in tetrahydrofuran

10 h; Heating;

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Rx-ID: 2768176 Find similar reactions

Gynther, Jukka; Peura, Pekka; Salmi, Seija

Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1985 , vol. 39, # 10 p. 849 - 860 Title/Abstract Full Text Show Details

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Multi-step reaction with 3 steps

Synthesize Find similar Gynther, Jukka; Peura, Pekka; Salmi, Seija

Rx-ID: 19064276 Find similar reactions

1: 88 percent / diethyl ether / 0.25 h / Ambient temperature 2: 96 percent / ammonia (gas) / toluene 3: 34 percent / lithium aluminium deuteride / tetrahydrofuran / 10 h / Heating View Scheme

Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1985 , vol. 39, # 10 p. 849 - 860 Title/Abstract Full Text Show Details

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Multi-step reaction with 2 steps 1: 96 percent / ammonia (gas) / toluene 2: 34 percent / lithium aluminium deuteride / tetrahydrofuran / 10 h / Heating View Scheme

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Rx-ID: 19069392 Find similar reactions

Gynther, Jukka; Peura, Pekka; Salmi, Seija

Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1985 , vol. 39, # 10 p. 849 - 860 Title/Abstract Full Text Show Details

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Rx-ID: 39059045 Find similar reactions

in methanol; diethyl ether

T=20°C; 60 h; Hide Experimental Procedure

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Blough, Bruce E.; Landavazo, Antonio; Partilla, John S.; Decker, Ann M.; Page, Kevin M.; Baumann, Michael H.; Rothman, Richard B.

Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 19 p. 4754 - 4758 Title/Abstract Full Text View citing articles Show Details

2-(4-Fluoro-1H-indol-3-yl)ethylamine Fumarate (4e).

General procedure: To a solution of 4’-Fluoro-2,3-di-oxotryptamine (3b, 644 mg, 3.12 mmol) in THF (30 mL), a 1.0 M LiAlH4/THF solution (16 mL, 16 mmol) was added slowly and the mixture was refluxed for 18 h. The reaction was quenched with water/THF (1/1) and made basic (pH 10) with 3 N aqueous NaOH. The solids were filtered through Celite; the filtrate was dried with anhydrous MgSO4 and concentrated. The crude material was purified by automated flash chromatography (silica gel, 20percent MeOH/DCM) to obtain 130 mg of colorless oil (23percent). This material was dissolved in diethyl ether (100 mL) and MeOH (1 mL) and a solution of Fumaric Acid (90 mg, 0.77 mmol) in MeOH (9 mL) was added. The reaction stirred at room temperature for 60 h and the resulting solids were filtered, washed with ether and dried. The dry solids were recrystallized (MeOH/ethyl acetate) to yield 70.3 mg of product

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Rx-ID: 8367651 Find similar reactions

Grandberg; Bobrova

Chemistry of Heterocyclic Compounds (New York, NY, United States), 1973 , vol. 9, p. 196,199 Khimiya Geterotsiklicheskikh Soedinenii, 1973 , vol. 9, p. 213 Full Text Show Details