2-(1H-indol-3-yl)-N,N-dimethylethan-1-amine (DMT) by Asch

Query Query

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Date

50 reactions in Reaxys

2016-06-01 12h:59m:07s (EST)

1. Query

Search as: As drawn

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NH O

NH 2

Rx-ID: 29607979 View in Reaxys 1/50 Yield 95 %

Conditions & References 4.2.1. General procedure for the preparation of compounds 2a-m General procedure: A stirred solution of tryptamine (1a) (200 mg, 1.25 mmol) in anhydrous methanol (20 mL) was added glacial acetic acid (280 μL, 4.99 mmol) followed by sodium cyanoborohydride (157 mg, 2.50 mmol) under Ar2 at 0 °C. A solution of formaldehyde (38percent, 220 μL, 3.00 mmol) or other appropriate aldehydes (3.00 mmol) in anhydrous methanol (15 mL) was then added dropwise over 20 min, and the resulting solution was stirred at room temperature for 2-16 h. Aqueous Na2CO3 (2 N) was added to adjust pH to 8-9 and the methanol was removed under reduce pressure. The residue was partitioned between CHCl3 and water. The organic layer was washed with water and brine, dried over Na2SO4, and concentrated in vacuum. The crude product was purified by CC of silica gel with gradient CHCl3/MeOH as eluant afforded compounds 2a-m. With sodium cyanoborohydride, acetic acid in methanol, T= 0 - 20 °C , Inert atmosphere Qu, Shi-Jin; Wang, Gui-Feng; Duan, Wen-Hu; Yao, Shan-Yan; Zuo, Jian-Ping; Tan, Chang-Heng; Zhu, DaYuan; Bioorganic and Medicinal Chemistry; vol. 19; nb. 10; (2011); p. 3120 - 3127 View in Reaxys

92 %

Stage 1: With sodium tetrahydroborate in tetrahydrofuran, T= 0 °C Stage 2: With sulfuric acid in tetrahydrofuran, water Stage 3: With sodium hydroxide in tetrahydrofuran, water, pH= 14 Moura, Sidnei; Carvalho, Felipe Garcia; de Oliveira, Carolina Dizioli Rodrigues; Pinto, Ernani; Yonamine, Mauricio; Phytochemistry Letters; vol. 3; nb. 2; (2010); p. 79 - 83 View in Reaxys

90.2 %

2-(1H-indol-3-yl)-N, N-dimethylethanamine (9) Asolution of 37percent formaldehyde (147.0 ml, 2000.0 mmol) in MeOH (80.0 ml) and asolution of NaBH4 (23.6 g, 625.0 mmol) in H2O (210.0 ml) were added dropwise, simultaneously, at 15 °C to a well-stirred solution of tryptamine (20.0 g, 125.0 mmol) in MeOH (320.0 ml). The mixture was stirred atroom temperature for 30 min. Then , the solution was adjusted to pH 9 byaddition of 10percent aqueous Na2CO3. MeOH was removed bydistillation and the product was extracted with ethyl acetate (3×100 ml). Thenthe organic layer was washed with brine, dried over Na2SO4,concentrated under reduced pressure. The residuewas recrystallized with ethyl acetate-hexane (5:1) to give 9 asa light brown solid (yield 21.2 g,90.2percent). Mp46~47 . 1H NMR (400 MHz,CDCl3): δ = 2.35 (s, 6H), 2.64~2.68 (m, 2H), 2.94~2.98 (m, 2H), 7.00(s, 1H), 7.12 (t, 1H, J =7.6 Hz), 7.18 (t, 1H, J =7.6 Hz), 7.34 (d, 1H, J =8.0 Hz), 7.62 (d, 1H, J =8.0 Hz), 8.15 (br s, 1H). 13C NMR (100 MHz, CDCl3): δ = 23.52, 45.22, 60.24, 111.13, 113.87, 118.67, 119.11, 121.64, 121.85,127.39, 136.32. ESI-MS (m/z): Calcd.:188.13; Found: 189.27[M+H]+. Anal. Calcd. for C12H16N2: C, 76.55percent;H, 8.57percent; N, 14.88percent. Found: C, 76.57percent; H, 8.61percent; N, 14.86percent. With sodium tetrahydroborate in methanol, water, Time= 0.5h, T= 15 - 20 °C , pH= 9 He, Yi; Li, Xiaolong; Li, Jue; Li, Xiaocen; Guo, Li; Hai, Li; Wu, Yong; Tetrahedron Letters; vol. 55; nb. 29; (2014); p. 3938 - 3941 View in Reaxys With sodium cyanoborohydride, acetic acid in methanol, Time= 2h, pH= 6.5, 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; vol. 27; nb. 3; (2012); p. 443 - 450 View in Reaxys

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N H N

Rx-ID: 113805 View in Reaxys 2/50 Yield

Conditions & References

84 %

5 :To 250 mg of 3 (2- bromoethyl)indole in a round-bottomed flask, a 10 M excess of dimethyiamine (6 mL of 2M in MeOH) was added and the solution was stirred at r.t. overnight. After adding 5 mL sodium bicarbonate (2percent), the reaction mixture was extracted with chloroform (3x5 ml) and back extracted with H2O (lx5mL). The combined extracts were dried over MgSO4 and evaporation of the solvent gave the product in crystalline form. Yield: 0.21 g, 84percent, yellowish crystals, m.p.: 45-47 0C; TLC (EtAc:MeOH: acetic acid, 8:2:0.5 v/v/v): RF = 0.33. H NMR, δ: 10.43 (s, 1 H), 7.42-7.06 (m, 5 H), 2.68 (m, 4H), 2.26 (S, 6 H). 13C NMR (CDCl3): δ 136.5, 124.3, 123.2, 121.2, 119.7, 117.6, 113.4, 111.1, 61.7, 41.2, 22.4. Anal, calcd for C12H16N2: C, 76.55; H, 8.57; N, 14.88percent. Found; C, 76.60; H, 8.70; N, 14.70percent. in methanol, T= 20 °C Patent; Wisconsin Alumni Research Foundation; RUOHO, Arnold E.; HAJIPOUR, Abdol R.; CHU, Uyen B.; FONTANILLA, Dominique A.; WO2010/59711; (2010); (A1) English View in Reaxys Vitali; Mossini; Bollettino Scientifico della Facolta di Chimica Industriale di Bologna; vol. 17; (1959); p. 84,86 View in Reaxys Hoshino; Shimodaira; Justus Liebigs Annalen der Chemie; vol. 520; (1935); p. 19,26 View in Reaxys

HN H 2N

Rx-ID: 9974992 View in Reaxys 3/50 Yield

Conditions & References

80 %

Stage 1: With hydrogen, 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene, Rh(acac)2(CO)2 in tetrahydrofuran, Time= 72h, T= 70 °C , p= 15001.2Torr Stage 2: With sulfuric acid, Time= 2h, Heating Schmidt, Axel M.; Eilbracht, Peter; Journal of Organic Chemistry; vol. 70; nb. 14; (2005); p. 5528 - 5535 View in Reaxys

O N

Rx-ID: 187377 View in Reaxys 4/50 Yield 76 %

Conditions & References With lithium aluminium tetrahydride in tetrahydrofuran, dichloromethane, Time= 48h, Ambient temperature Sintas, Jose A.; Vitale, Arturo A.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 39; nb. 8; (1997); p. 677 - 684 View in Reaxys

46 %

With lithium aluminium tetrahydride in 1,4-dioxane, T= 100 °C Celik, Leyla; Sinning, Steffen; Severinsen, Kasper; Hansen, Carsten G.; Moller, Maria S.; Bols, Mikael; Wiborg, Ove; Schiott, Birgit; Journal of the American Chemical Society; vol. 130; nb. 12; (2008); p. 3853 - 3865 View in Reaxys

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With lithium aluminium tetrahydride Fish et al.; Journal of the American Chemical Society; vol. 78; (1956); p. 3668,3670 View in Reaxys

N HO

N N

N O

NH 2

Rx-ID: 24517071 View in Reaxys 5/50 Yield

Conditions & References

87%

3.3 : 3. 3. N,N-Dimethyl-2-[5-(2-methyltetrazol-5-ylmethyl)-1H-indol-3-yl]ethylamine.Oxalate A solution of formaldehyde (80 mg of a 30percent solution) in methanol (15 ml) was added to a stirred solution of 2[5-(2-methyltetrazol-5-ylmethyl)-1H-indol-3-yl]ethylamine (0.1 g, 0.4 mmol), NaCNBH3 (60 mg) and glacial acetic acid (0.12 g) in methanol (15 ml). The solution was stirred for 2 h, basified with K2 CO3 solution and the MeOH removed under vacuum. The crude product obtained after extraction into ethylacetate and removal of solvent was chromatographed through silica-gel eluding with CH2 Cl2 /EtOH/NH3 (40:8:1) to give the desired N,N-dimethyltryptamine (96 mg, 87percent). The oxalate salt was prepared: mp 185°-187° C. (MeOH/Et2 O); (Found: C, 54.42; H, 5.74; N, 22.53. C15 H20 N6.C2 H2 O4 requires C, 54.54; H, 5.92; N, 22.45percent); δ (360 MHz, D2 O) 2.91 (6H, s, 2 of CH3); 3.21 (2H, t, J=7.4 Hz, CH2); 3.47 (2H, J=7.4 Hz, CH2); 4.30 (3H, s, CH3); 4.34 (2H, s, CH2); 7.17 (1H, dd, J=1.5 and 8.4 Hz, Ar-H); 7.33 (1H, s, Ar-H); 7.48 (1H, d, J=8.4 Hz, Ar-H); 7.59 (1H, s, Ar-H). With formaldehyd, NaCNBH3 in methanol, acetic acid Patent; Merck Sharp and Dohme Limited; US5298520; (1994); (A1) English View in Reaxys

Rx-ID: 2549251 View in Reaxys 6/50 Yield

Conditions & References

100 %

With hydrogen, palladium on activated charcoal in methanol, Time= 18h Djura; Stierle; Sullivan; et al.; Journal of Organic Chemistry; vol. 45; nb. 8; (1980); p. 1435 - 1441 View in Reaxys

Rx-ID: 2555211 View in Reaxys 7/50 Yield 100 %

Conditions & References With hydrogen, palladium on activated charcoal in methanol, Time= 18h Djura; Stierle; Sullivan; et al.; Journal of Organic Chemistry; vol. 45; nb. 8; (1980); p. 1435 - 1441 View in Reaxys

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NH O

H N

NH 2

Rx-ID: 35697177 View in Reaxys 8/50 Yield

Conditions & References 21 : [0508] Procedure for the synthesis of 2-(5-alkoxy-lH-indol-3-yl)-N,N- dimethylethanamine (KD38-KD46). [0508] Procedure for the synthesis of 2-(5-alkoxy-lH-indol-3-yl)-N,N- dimethylethanamine (KD38-KD46). [0509] The 3-(2-Aminoethyl)-5-(alkoxy)indole hydrogen chloride (0.5 mmol) was dissolved in MeOH (2.5 mL) along with sodium cyanoboron hydride (0.9 mmol), and acetic acid (1.35 mmol) in a 50 mL round bottom flask. The reaction mixture was stirred for 5 min. to obtain a homogenous solution and cooled to 0 oC in an ice bath. A solution of 37 percent formaldehyde (v/v in water) in MeOH (2.5 mL) was added via syringe to the cooled reaction mixture. The temperature was allowed to gradually raise to 25 oC and reaction continued at 25 oC for 12 h. The reaction was quenched with potassium carbonate (excess) and solvent evaporated. The residue obtained wad resuspended in water (10 mL) and extracted with EtOAc (2 x 5 mL). The EtOAc layer was washed with water (2 x 5 mL), brine (2 x 5 mL) and dried over sodium sulfate. The organic layer was evaporated under reduced pressure at 30 oC and dried to obtain the 3-(2-N,N- dimethylaminoethyl)-5-(alkoxy)indoles as pale yellow semi solid. Stage 1: With sodium cyanoborohydride, acetic acid in methanol, Time= 0.0833333h Stage 2: in methanol, water, Time= 12h, T= 0 - 25 °C Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; OZPOLAT, Bulent; LOPEZ-BERESTEIN, Gabriel; DALBY, Kevin N.; JOSE, Jiney; WO2013/63492; (2013); (A1) English View in Reaxys

NH 2 OH

Rx-ID: 11178277 View in Reaxys 9/50 Yield

Conditions & References

74 %

With potassium hydroxide, [{(η5-C5Me5)IrCl}2(μ-Cl)2], Time= 48h, T= 110 °C Whitneys, Simon; Grigg, Ronald; Derrick, Andrew; Keep, Ann; Organic Letters; vol. 9; nb. 17; (2007); p. 3299 3302 View in Reaxys

Rx-ID: 9097830 View in Reaxys 10/50 Yield 0.19 g

Conditions & References With diisobutylaluminium hydride, [1,3-bis(diphenylphosphino) propane] dichloronickel(II) in toluene, Time= 2h, T= 20 °C Barluenga, Jose; Fananas, Francisco J.; Sanz, Roberto; Fernandez, Yolanda; Chemistry - A European Journal; vol. 8; nb. 9; (2002); p. 2034 - 2046 View in Reaxys

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O O

N 2H

Rx-ID: 11192118 View in Reaxys 11/50 Yield

Conditions & References

89 %

With lithium aluminium deuteride in tetrahydrofuran Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368 View in Reaxys

80 %

With lithium aluminium deuteride in tetrahydrofuran, Inert atmosphere, Microwave irradiation Brandt, Simon D.; Tirunarayanapuram, Sri Subha; Freeman, Sally; Dempster, Nicola; Barker, Steven A.; Daley, Paul F.; Cozzi, Nicholas V.; Martins, Claudia P. B.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 51; nb. 14; (2008); p. 423 - 429 View in Reaxys

O N

Rx-ID: 40957418 View in Reaxys 12/50 Yield

Conditions & References

55 %

With hydrogenchloride, titanium(III) chloride in water, acetonitrile, Time= 8h, T= 20 °C , Inert atmosphere Tong, Shuo; Xu, Zhengren; Mamboury, Mathias; Wang, Qian; Zhu, Jieping; Angewandte Chemie - International Edition; vol. 54; nb. 40; (2015); p. 11809 - 11812; Angew. Chem.; vol. 127; nb. 40; (2015); p. 11975 - 11978,4 View in Reaxys

NH HO

NH 2

Rx-ID: 41801037 View in Reaxys 13/50 Yield

Conditions & References

89 %

With formaldehyd, nitrogen, sodium cyanoborohydride, acetic acid, Time= 24h, T= 0 - 20 °C Olsen, Elisabeth K.; Hansen, Espen; Moodie, Lindon W. K.; Isaksson, Johan; Sepi, Kristina; Cergolj, Marija; Svenson, Johan; Andersen, Jeanette H.; Organic and Biomolecular Chemistry; vol. 14; nb. 5; (2016); p. 1629 1640 View in Reaxys

H N

Rx-ID: 14728007 View in Reaxys 14/50 Yield

Conditions & References Reaction Steps: 3 1.1: BuLi / hexane; tetrahydrofuran / 1 h / -50 - 20 °C 1.2: 71 percent / hexane; tetrahydrofuran / 5.25 h 2.1: t-BuLi / tetrahydrofuran; pentane / 0.05 h / -110 - -40 °C 2.2: H2O / tetrahydrofuran; pentane / 20 °C

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2.3: tetrahydrofuran; pentane / 3 h / 67 °C 3.1: 0.19 g / DIBAL-H / [NiCl2(dppp)] / toluene / 2 h / 20 °C With n-butyllithium, tert.-butyl lithium, diisobutylaluminium hydride, [1,3-bis(diphenylphosphino) propane] dichloronickel(II) in tetrahydrofuran, hexane, toluene, pentane Barluenga, Jose; Fananas, Francisco J.; Sanz, Roberto; Fernandez, Yolanda; Chemistry - A European Journal; vol. 8; nb. 9; (2002); p. 2034 - 2046 View in Reaxys

H 2N

F N

Rx-ID: 14729960 View in Reaxys 15/50 Yield

Conditions & References Reaction Steps: 5 1.1: BuLi / hexane; tetrahydrofuran / 1.25 h / -50 - 20 °C 1.2: 80 percent / hexane; tetrahydrofuran / 5.25 h 2.1: BuLi / hexane; tetrahydrofuran / 1.25 h / -50 - 20 °C 2.2: 75 percent / hexane; tetrahydrofuran / 5.25 h 3.1: BuLi / hexane; tetrahydrofuran / 1 h / -50 - 20 °C 3.2: 71 percent / hexane; tetrahydrofuran / 5.25 h 4.1: t-BuLi / tetrahydrofuran; pentane / 0.05 h / -110 - -40 °C 4.2: H2O / tetrahydrofuran; pentane / 20 °C 4.3: tetrahydrofuran; pentane / 3 h / 67 °C 5.1: 0.19 g / DIBAL-H / [NiCl2(dppp)] / toluene / 2 h / 20 °C With n-butyllithium, tert.-butyl lithium, diisobutylaluminium hydride, [1,3-bis(diphenylphosphino) propane] dichloronickel(II) in tetrahydrofuran, hexane, toluene, pentane Barluenga, Jose; Fananas, Francisco J.; Sanz, Roberto; Fernandez, Yolanda; Chemistry - A European Journal; vol. 8; nb. 9; (2002); p. 2034 - 2046 View in Reaxys

NH F HN

Rx-ID: 14735576 View in Reaxys 16/50 Yield

Conditions & References Reaction Steps: 4 1.1: BuLi / hexane; tetrahydrofuran / 1.25 h / -50 - 20 °C 1.2: 75 percent / hexane; tetrahydrofuran / 5.25 h 2.1: BuLi / hexane; tetrahydrofuran / 1 h / -50 - 20 °C 2.2: 71 percent / hexane; tetrahydrofuran / 5.25 h 3.1: t-BuLi / tetrahydrofuran; pentane / 0.05 h / -110 - -40 °C 3.2: H2O / tetrahydrofuran; pentane / 20 °C 3.3: tetrahydrofuran; pentane / 3 h / 67 °C 4.1: 0.19 g / DIBAL-H / [NiCl2(dppp)] / toluene / 2 h / 20 °C With n-butyllithium, tert.-butyl lithium, diisobutylaluminium hydride, [1,3-bis(diphenylphosphino) propane] dichloronickel(II) in tetrahydrofuran, hexane, toluene, pentane Barluenga, Jose; Fananas, Francisco J.; Sanz, Roberto; Fernandez, Yolanda; Chemistry - A European Journal; vol. 8; nb. 9; (2002); p. 2034 - 2046 View in Reaxys

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F N Br

Rx-ID: 14754286 View in Reaxys 17/50 Yield

Conditions & References Reaction Steps: 2 1.1: t-BuLi / tetrahydrofuran; pentane / 0.05 h / -110 - -40 °C 1.2: H2O / tetrahydrofuran; pentane / 20 °C 1.3: tetrahydrofuran; pentane / 3 h / 67 °C 2.1: 0.19 g / DIBAL-H / [NiCl2(dppp)] / toluene / 2 h / 20 °C With tert.-butyl lithium, diisobutylaluminium hydride, [1,3-bis(diphenylphosphino) propane] dichloronickel(II) in tetrahydrofuran, toluene, pentane Barluenga, Jose; Fananas, Francisco J.; Sanz, Roberto; Fernandez, Yolanda; Chemistry - A European Journal; vol. 8; nb. 9; (2002); p. 2034 - 2046 View in Reaxys

O O

Rx-ID: 254956 View in Reaxys 18/50 Yield

Conditions & References

70 %

With lithium aluminium tetrahydride Somei, Masanori; Kobayashi, Kensuke; Tanii, Keiko; Mochizuki, Toshihiko; Kawada, Yumiko; Fukui, Yoshikazu; Heterocycles; vol. 40; nb. 1; (1995); p. 119 - 122 View in Reaxys With lithium aluminium tetrahydride Kondo et al.; ; Labor Nr. 10 <1959> 1, 8; engl. Ausg. S. 33, 42 View in Reaxys With lithium aluminium tetrahydride in diethyl ether, benzene, Time= 2h, Heating, Reduction Haefelinger, Guenter; Nimtz, Manfred; Horstmann, Volker; Benz, Thomas; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 54; nb. 3; (1999); p. 397 - 414 View in Reaxys With lithium aluminium tetrahydride in 1,4-dioxane, Reflux Chu, Uyen B.; Vorperian, Sevahn K.; Satyshur, Kenneth; Eickstaedt, Kelsey; Cozzi, Nicholas V.; Mavlyutov, Timur; Hajipour, Abdol R.; Ruoho, Arnold E.; Biochemistry; vol. 53; nb. 18; (2014); p. 2956 - 2965 View in Reaxys

N O

H 2N N

Rx-ID: 2028955 View in Reaxys 19/50 Yield 86 %

Conditions & References With sulfuric acid, Time= 2h, Heating Chen; Senanayake; Bill; Larsen; Verhoeven; Reider; Journal of Organic Chemistry; vol. 59; nb. 13; (1994); p. 3738 - 3741

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View in Reaxys

NH 2

Rx-ID: 9182501 View in Reaxys 20/50 Yield

Conditions & References Stage 1: With vinylsulfonylmethyl polystyrene in N,N-dimethyl-formamide Stage 2: in N,N-dimethyl-formamide Stage 3: With N-ethyl-N,N-diisopropylamine in dichloromethane, Hoffman elimination, Further stages. Wu, Tom Y. H.; Schulte, Peter G.; Organic Letters; vol. 4; nb. 23; (2002); p. 4033 - 4035 View in Reaxys

NH N

Rx-ID: 40157409 View in Reaxys 21/50 Yield

Conditions & References

42 %

With [Cp*IrCl2]2, caesium carbonate, Time= 48h, T= 150 °C , Inert atmosphere, Sealed tube Bartolucci, Silvia; Mari, Michele; Bedini, Annalida; Piersanti, Giovanni; Spadoni, Gilberto; Journal of Organic Chemistry; vol. 80; nb. 6; (2015); p. 3217 - 3222 View in Reaxys

Rx-ID: 16997062 View in Reaxys 22/50 Yield

Conditions & References Reaction Steps: 2 1: Na2WO4, H2O2 2: 16 percent / 5percent aq. H2SO4 / 6 h / Heating With sodium tungstate, sulfuric acid, dihydrogen peroxide Somei, Masanori; Yamada, Fumio; Morikawa, Harunobu; Heterocycles; vol. 46; (1997); p. 91 - 94 View in Reaxys Reaction Steps: 2 1: 55 percent / Na2WO4*2H2O, 30percent H2O2 / methanol; H2O 2: 11 percent / 47percent aq. HBr / 1 h / Ambient temperature With sodium tungstate, hydrogen bromide, dihydrogen peroxide in methanol, water Somei, Masanori; Kobayashi, Kensuke; Tanii, Keiko; Mochizuki, Toshihiko; Kawada, Yumiko; Fukui, Yoshikazu; Heterocycles; vol. 40; nb. 1; (1995); p. 119 - 122 View in Reaxys

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NH Br N

Rx-ID: 20823541 View in Reaxys 23/50 Yield

Conditions & References Reaction Steps: 3 1: diethyl ether / 0 °C 2: H2O / 0.5 h 3: LiAlH4 / dioxane / 3 h / Heating With lithium aluminium tetrahydride in 1,4-dioxane, diethyl ether, water Tymiak; Rinehart Jr.; Bakus; Tetrahedron; vol. 41; nb. 6; (1985); p. 1039 - 1047 View in Reaxys

NH Br

O O

Rx-ID: 20833566 View in Reaxys 24/50 Yield

Conditions & References Reaction Steps: 2 1: H2O / 0.5 h 2: LiAlH4 / dioxane / 3 h / Heating With lithium aluminium tetrahydride in 1,4-dioxane, water Tymiak; Rinehart Jr.; Bakus; Tetrahedron; vol. 41; nb. 6; (1985); p. 1039 - 1047 View in Reaxys

Rx-ID: 2765443 View in Reaxys 25/50 Yield

Conditions & References With lithium aluminium tetrahydride in diethyl ether, Time= 2h, Heating, Yield given Mahboobi; Grothus; Meindl; Archiv der Pharmazie; vol. 327; nb. 2; (1994); p. 105 - 114 View in Reaxys

O O

Rx-ID: 2841167 View in Reaxys 26/50 Yield

Conditions & References With lithium aluminium tetrahydride in 1,4-dioxane, Time= 3h, Heating Tymiak; Rinehart Jr.; Bakus; Tetrahedron; vol. 41; nb. 6; (1985); p. 1039 - 1047 View in Reaxys

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O N

Rx-ID: 17028314 View in Reaxys 27/50 Yield

Conditions & References Reaction Steps: 3 1: 95 percent / concd. H2SO4 / 2 h / Heating 2: 80 percent / H2O / 40 h / 20 °C 3: 76 percent / LiAlH4 / CH2Cl2; tetrahydrofuran / 48 h / Ambient temperature With lithium aluminium tetrahydride, sulfuric acid in tetrahydrofuran, dichloromethane, water Sintas, Jose A.; Vitale, Arturo A.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 39; nb. 8; (1997); p. 677 - 684 View in Reaxys

O N

Rx-ID: 17028662 View in Reaxys 28/50 Yield

Conditions & References Reaction Steps: 2 1: 80 percent / H2O / 40 h / 20 °C 2: 76 percent / LiAlH4 / CH2Cl2; tetrahydrofuran / 48 h / Ambient temperature With lithium aluminium tetrahydride in tetrahydrofuran, dichloromethane, water Sintas, Jose A.; Vitale, Arturo A.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 39; nb. 8; (1997); p. 677 - 684 View in Reaxys

NH 2

Rx-ID: 18689793 View in Reaxys 29/50 Yield

Conditions & References Reaction Steps: 4 1: diethyl ether / from 0 deg C up to r.t. 2: LiAlH4 / diethyl ether / 2 h / Heating 3: diethyl ether / from 0 deg C up to r.t. 4: LiAlH4 / diethyl ether / 2 h / Heating With lithium aluminium tetrahydride in diethyl ether Mahboobi; Grothus; Meindl; Archiv der Pharmazie; vol. 327; nb. 2; (1994); p. 105 - 114 View in Reaxys

Rx-ID: 18690239 View in Reaxys 30/50

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Yield

Conditions & References Reaction Steps: 2 1: diethyl ether / from 0 deg C up to r.t. 2: LiAlH4 / diethyl ether / 2 h / Heating With lithium aluminium tetrahydride in diethyl ether Mahboobi; Grothus; Meindl; Archiv der Pharmazie; vol. 327; nb. 2; (1994); p. 105 - 114 View in Reaxys

Rx-ID: 18690889 View in Reaxys 31/50 Yield

Conditions & References Reaction Steps: 3 1: LiAlH4 / diethyl ether / 2 h / Heating 2: diethyl ether / from 0 deg C up to r.t. 3: LiAlH4 / diethyl ether / 2 h / Heating With lithium aluminium tetrahydride in diethyl ether Mahboobi; Grothus; Meindl; Archiv der Pharmazie; vol. 327; nb. 2; (1994); p. 105 - 114 View in Reaxys

NH 2H

(+-)-2-butyl-octan-1-ol

N 2H

Rx-ID: 11300933 View in Reaxys 32/50 Yield

Conditions & References Reaction Steps: 3 1: diethyl ether / 4 h / 0 - 20 °C 2: 92 percent / aq. NaOH / diethyl ether / 0.5 h 3: 89 percent / LiAlD4 / tetrahydrofuran With sodium hydroxide, lithium aluminium deuteride in tetrahydrofuran, diethyl ether Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368 View in Reaxys

O O

N 2H

Rx-ID: 11321731 View in Reaxys 33/50 Yield

Conditions & References Reaction Steps: 2 1: 92 percent / aq. NaOH / diethyl ether / 0.5 h 2: 89 percent / LiAlD4 / tetrahydrofuran With sodium hydroxide, lithium aluminium deuteride in tetrahydrofuran, diethyl ether Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368 View in Reaxys

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(2-fluorotoluene)Cr(CO)3 N

Rx-ID: 16039048 View in Reaxys 34/50 Yield

Conditions & References Reaction Steps: 3 1: diethyl ether / 0.17 h 2: diethyl ether / 0.17 h 3: LiAlH4 / diethyl ether; benzene / 2 h / Heating With lithium aluminium tetrahydride in diethyl ether, benzene, 1: Acylation / 2: Substitution / 3: Reduction Haefelinger, Guenter; Nimtz, Manfred; Horstmann, Volker; Benz, Thomas; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 54; nb. 3; (1999); p. 397 - 414 View in Reaxys

O O

Rx-ID: 16040406 View in Reaxys 35/50 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether / 0.17 h 2: LiAlH4 / diethyl ether; benzene / 2 h / Heating With lithium aluminium tetrahydride in diethyl ether, benzene, 1: Substitution / 2: Reduction Haefelinger, Guenter; Nimtz, Manfred; Horstmann, Volker; Benz, Thomas; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 54; nb. 3; (1999); p. 397 - 414 View in Reaxys

Rx-ID: 38137718 View in Reaxys 36/50 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether / 0 °C / pH 9 - 10 2: lithium aluminium tetrahydride / 1,4-dioxane / |Reflux With lithium aluminium tetrahydride in 1,4-dioxane, diethyl ether Chu, Uyen B.; Vorperian, Sevahn K.; Satyshur, Kenneth; Eickstaedt, Kelsey; Cozzi, Nicholas V.; Mavlyutov, Timur; Hajipour, Abdol R.; Ruoho, Arnold E.; Biochemistry; vol. 53; nb. 18; (2014); p. 2956 - 2965 View in Reaxys

O N

Rx-ID: 40957414 View in Reaxys 37/50 Yield

Conditions & References Reaction Steps: 2

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1: tetrahydrofuran; methanol / 48 h / 20 °C / |Inert atmosphere 2: titanium(III) chloride; hydrogenchloride / water; acetonitrile / 8 h / 20 °C / |Inert atmosphere With hydrogenchloride, titanium(III) chloride in tetrahydrofuran, methanol, water, acetonitrile Tong, Shuo; Xu, Zhengren; Mamboury, Mathias; Wang, Qian; Zhu, Jieping; Angewandte Chemie - International Edition; vol. 54; nb. 40; (2015); p. 11809 - 11812; Angew. Chem.; vol. 127; nb. 40; (2015); p. 11975 - 11978,4 View in Reaxys

OH O

Rx-ID: 40957481 View in Reaxys 38/50 Yield

Conditions & References Reaction Steps: 3 1: triphenylphosphine; carbon tetrabromide / dichloromethane / 2 h / 20 °C / |Inert atmosphere 2: tetrahydrofuran; methanol / 48 h / 20 °C / |Inert atmosphere 3: titanium(III) chloride; hydrogenchloride / water; acetonitrile / 8 h / 20 °C / |Inert atmosphere With hydrogenchloride, titanium(III) chloride, carbon tetrabromide, triphenylphosphine in tetrahydrofuran, methanol, dichloromethane, water, acetonitrile Tong, Shuo; Xu, Zhengren; Mamboury, Mathias; Wang, Qian; Zhu, Jieping; Angewandte Chemie - International Edition; vol. 54; nb. 40; (2015); p. 11809 - 11812; Angew. Chem.; vol. 127; nb. 40; (2015); p. 11975 - 11978,4 View in Reaxys O NH

(v5)

Rx-ID: 3609423 View in Reaxys 39/50 Yield

Conditions & References With ammonium hydroxide, iron(II) sulfate, Time= 0.5h, Heating Kawanishi, K.; Uhara, Y.; Hashimoto, Y.; Phytochemistry (Elsevier); vol. 24; nb. 6; (1985); p. 1373 - 1376 View in Reaxys OH

NH Br

Rx-ID: 4096943 View in Reaxys 40/50 Yield 2 %, 11 %, 25 %

Conditions & References With hydrogen bromide, Time= 1h, Ambient temperature Somei, Masanori; Kobayashi, Kensuke; Tanii, Keiko; Mochizuki, Toshihiko; Kawada, Yumiko; Fukui, Yoshikazu; Heterocycles; vol. 40; nb. 1; (1995); p. 119 - 122 View in Reaxys

25 %, 11 %, 2 %

With hydrogen bromide, Time= 1h, Ambient temperature Somei, Masanori; Kobayashi, Kensuke; Tanii, Keiko; Mochizuki, Toshihiko; Kawada, Yumiko; Fukui, Yoshikazu; Heterocycles; vol. 40; nb. 1; (1995); p. 119 - 122 View in Reaxys

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F F

O HN

O– O

F F

N+

Rx-ID: 9183169 View in Reaxys 41/50 Yield

Conditions & References Stage 1:T= 90 - 100 °C Stage 2: in water, acetonitrile Altamura, Maria; Canfarini, Franca; Catalioto, Rose-Marie; Guidi, Antonio; Pasqui, Franco; Renzetti, Anna R.; Triolo, Antonio; Maggi, Carlo A.; Bioorganic and Medicinal Chemistry Letters; vol. 12; nb. 20; (2002); p. 2945 2948 View in Reaxys OH

Rx-ID: 4893811 View in Reaxys 42/50 Yield

Conditions & References

16 %, 47 %

With sulfuric acid, Time= 6h, Heating Somei, Masanori; Yamada, Fumio; Morikawa, Harunobu; Heterocycles; vol. 46; (1997); p. 91 - 94 View in Reaxys

Rx-ID: 4019531 View in Reaxys 43/50 Yield

Conditions & References With butane-1-thiol in tetrachloromethane, T= 25 °C , Rate constant Tupitsyn, I. F.; Komarov, V. I.; J. Gen. Chem. USSR (Engl. Transl.); vol. 57; nb. 8; (1987); p. 1826 - 1835,1632 1640 View in Reaxys

(+-)-indolin-3-ol N

Rx-ID: 18049049 View in Reaxys 44/50 Yield

Conditions & References Reaction Steps: 2 1: 87 percent

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2: 70 percent / LiAlH4 With lithium aluminium tetrahydride Somei, Masanori; Kobayashi, Kensuke; Tanii, Keiko; Mochizuki, Toshihiko; Kawada, Yumiko; Fukui, Yoshikazu; Heterocycles; vol. 40; nb. 1; (1995); p. 119 - 122 View in Reaxys

Rx-ID: 22170181 View in Reaxys 45/50 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether; phosphorus (III)-bromide With diethyl ether, phosphorus tribromide Hoshino; Shimodaira; Justus Liebigs Annalen der Chemie; vol. 520; (1935); p. 19,26 View in Reaxys OH

HO N

Rx-ID: 4858419 View in Reaxys 46/50 Yield

Conditions & References

7 %, 11 %, 57 %

With sulfuric acid, Heating Somei, Masanori; Yamada, Fumio; Morikawa, Harunobu; Heterocycles; vol. 46; (1997); p. 91 - 94 View in Reaxys

Cl – N+

Rx-ID: 543200 View in Reaxys 47/50 Yield

Conditions & References Manske; Canadian Journal of Research; vol. 5; (1931); p. 599; Chem. Zentralbl.; vol. 103; nb. I; (1932); p. 2475 View in Reaxys

Rx-ID: 5437601 View in Reaxys 48/50 Yield

Conditions & References Hall; McCapra; Scott; Tetrahedron; vol. 23; nb. 10; (1967); p. 4131 - 4141 View in Reaxys Fleming,I.; Woolias,M.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1979); p. 829 - 837 View in Reaxys Noell et al.; Journal of Heterocyclic Chemistry; vol. 3; (1966); p. 5,9

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View in Reaxys Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; ; vol. 60; nb. 13215b; (1964) View in Reaxys Ganellin et al.; Journal of the Chemical Society [Section] C: Organic; (1967); p. 2220 View in Reaxys Noland; Sundberg; Journal of Organic Chemistry; vol. 28; (1963); p. 884 View in Reaxys Morimoto et al.; Justus Liebigs Annalen der Chemie; vol. 682; (1965); p. 212,218 View in Reaxys Julia et al.; Bulletin de la Societe Chimique de France; (1973); p. 1424 View in Reaxys Bodendorf; Walk; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 294; (1961); p. 484,487 View in Reaxys Wenkert; Kryger; Journal of the Indian Chemical Society; vol. 55; (1978); p. 1122 View in Reaxys Ghosal; Mazumder; Phytochemistry (Elsevier); vol. 10; (1971); p. 2840 View in Reaxys Illustrative examples of such compounds includes: ... 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; N,N-dimethyltryptamine; and Patent; Eli Lilly and Company; US5096908; (1992); (A1) English View in Reaxys Patent; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; KOZIKOWSKI, Alan; KALIN, Jay, Hans; BUTLER, Kyle, Vincent; BERGMAN, Joel; HANCOCK, Wayne, W.; WO2012/106343; (2012); (A2) English View in Reaxys

NH 14CH

Rx-ID: 5601184 View in Reaxys 49/50 Yield

Conditions & References <2-14C>-Indol, 1.) Oxalylchlorid, 2.) Dimethylamid, 3.) LiAlH4 Baxter; Slaytor; Phytochemistry (Elsevier); vol. 11; (1972); p. 2767,2773 View in Reaxys

15NH

Rx-ID: 5601185 View in Reaxys 50/50 Yield

Conditions & References <1-15N>-N,N-Dimethyl-3-indolyloxalylamid, LiAlH4 Dmitrevskaya et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 9; (1973); p. 476; Khimiya Geterotsiklicheskikh Soedinenii; vol. 9; (1973); p. 516 View in Reaxys

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