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19 reactions in Reaxys
2016-04-19 04h:34m:43s (EST)
O NH 2
1. Query
O
Search as: As drawn
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O
O
O
O
N O
O
H 2N
Rx-ID: 363363 View in Reaxys 1/19 Yield 76 %
Conditions & References With lithium aluminium tetrahydride in tetrahydrofuran, Heating Cheng; Castagnoli Jr.; Journal of Medicinal Chemistry; vol. 27; nb. 4; (1984); p. 513 - 520 View in Reaxys With hydrochlorid acid, ethanol, acetic acid, bei der Reduktion an Blei-Elektroden Sugasawa; Shigehara; Chemische Berichte; vol. 74; (1941); p. 459,462 View in Reaxys With lithium aluminium tetrahydride, diethyl ether, T= 170 °C Cromartie; Harley-Mason; Journal of the Chemical Society; (1952); p. 2525 View in Reaxys Govindachari; Lakshmikantham; Proceedings - Indian Academy of Sciences, Section A; vol. <A> 46; (1957); p. 406,408 View in Reaxys With lithium aluminium tetrahydride in diethyl ether, benzene Khafagy,E.Z.; Lambooy,J.P.; Journal of Medicinal Chemistry; vol. 9; (1966); p. 936 - 940 View in Reaxys 2 : Example 2 Example 2 Preparation of 2-(2,5-dimethoxyphenyl)ethanamine 3 Lithium aluminum hydride (LiAlH4) (5.38g, 0.14mol) was added portion-wise to anhydrous tetrahydrofuran (250ml) and then (E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene 2 (9.87g, 0.047mol) dissolved in anhydrous tetrahydrofuran (150ml) was added drop-wise. The reaction mixture was refluxed for 4 hours then stirred at room temperature overnight. To quench the reaction mixture, water (5ml) followed by 1 M sodium hydroxide (5ml) and then water (15ml) were added slowly while cooling. The resulting mixture was then stirred at room temperature and the white precipitate which formed was removed by filtration through a celite plug and washed with Et2O. The solvent was removed under vacuo to give 5.76g of 2-(2,5-dimethoxyphenyl) ethanamine 3 crude as yellow oil. With sodium hydroxide in tetrahydrofuran, water Patent; Randox Laboratories Ltd.; Benchikh, Elouard; Fitzgerald, Peter; McConnell, Ivan; Lowry, Philip; EP2835648; (2015); (A1) English View in Reaxys
12.5 g
2 : Example 2 Example 2 Preparation of 2-(2, 5-dimethoxyphenyl)ethylamine 3 To lithium aluminium hydride (10.32 g, 0.27 mol) was added anhydrous THF (300 ml). A solution of 1-(2, 5-dimethoxyphenyl)nitroethane 2 (20.0 g, 0.956 mol) in THF (150 ml) was added drop-wise over a period of 45 min. The mixture was heated at reflux for 4 hours, after which thin-layer chromatography (TLC) analysis showed absence of starting material. After cooling at room temperature the reaction was quenched by the stepwise addition of 50percent THF/H2O (10 ml), 15percent NaOH solution and H2O (30 ml). The precipitate solids were removed by vacuum filtration, and the filtrate was reduced under vacuum to afford a yellow oil. The oil was dissolved in Et2O washed with H2O (2x 100 ml) and then extracted into 1 M HCl (2x 200 ml). The acidic extracts were washed with Et2O (2x 75 ml) and then made strongly basic with 5 M NaOH.
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The basic solution was extracted with Et2O (3x 150 ml). The ether extract was washed with water (2x 100 ml), and brine (100 ml) dried over Na2SO4 and filtered. The filtrate was concentrated to dryness to provide 12.5 g of 2-(2, 5-dimethoxyphenyl)ethylamine 3 as a clear oil. With lithium aluminium tetrahydride, sodium hydroxide in tetrahydrofuran, Time= 4.75h, Reflux Patent; Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan; EP2950104; (2015); (A1) English View in Reaxys
O O N
O
E
O
O
O
H 2N
Rx-ID: 2148479 View in Reaxys 2/19 Yield 31 %
Conditions & References With sodium tetrahydroborate, boron trifluoride diethyl etherate in tetrahydrofuran, Time= 4h, Heating Montgomery; Buon; Eibauer; Guiry; Keenan; McBean; British Journal of Pharmacology; vol. 152; nb. 7; (2007); p. 1121 - 1130 View in Reaxys With lithium aluminium tetrahydride, sulfuric acid in tetrahydrofuran, Time= 24h, Ambient temperature Croisy-Delcey, Martine; Huel, Christianne; Bisagni, Emile; Journal of Heterocyclic Chemistry; vol. 25; nb. 2; (1988); p. 655 - 660 View in Reaxys With lithium aluminium tetrahydride in tetrahydrofuran, Time= 4h, Ambient temperature Kubo, Akinori; Saito, Naoki; Kawakami, Nanko; Matsuyama, Yasuo; Miwa, Teruyo; Synthesis; nb. 9; (1987); p. 824 - 827 View in Reaxys With lithium aluminium tetrahydride in tetrahydrofuran, Time= 2h, Heating Cantrell, Amanda S.; Engelhardt, Per; Hoegberg, Marita; Jaskunas, S. Richard; Johansson, Nils Gunnar; Jordan, Christopher L.; Kangasmetsae, Jussi; Kinnick, Michael D.; Lind, Peter; Morin Jr., John M.; Muesing; Noreen, Rolf; Oeberg, Bo; Pranc, Paul; Sahlberg, Christer; Ternansky, Robert J.; Vasileff, Robert T.; Vrang, Lotta; West, Sarah J.; Zhang, Hong; Journal of Medicinal Chemistry; vol. 39; nb. 21; (1996); p. 4261 - 4274 View in Reaxys 2 : Preparation of 2-(2,5-dimethoxyphenyl)ethanamine 3 Example 2 Preparation of 2-(2,5-dimethoxyphenyl)ethanamine 3 Lithium aluminum hydride (LAIN (5.38 g, 0.14 mol) was added portion-wise to anhydrous tetrahydrofuran (250 ml) and then (E)-1,4-dimethoxy-2-(2-nitrovinyl)benzene 2 (9.87 g, 0.047 mol) dissolved in anhydrous tetrahydrofuran (150 ml) was added drop-wise. The reaction mixture was refluxed for 4 hours then stirred at room temperature overnight. To quench the reaction mixture, water (5 ml) followed by 1M sodium hydroxide (5 ml) and then water (15 ml) were added slowly while cooling. The resulting mixture was then stirred at room temperature and the white precipitate which formed was removed by filtration through a celite plug and washed with Et2O. The solvent was removed under vacuo to give 5.76 g of 2-(2,5-dimethoxyphenyl) ethanamine 3 crude as yellow oil. With sodium hydroxide in tetrahydrofuran, water Patent; Benchikh, Elouard; Fitzgerald, Peter; McConnell, Ivan; Lowry, Philip; US2015/38366; (2015); (A1) English View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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O
O
O
O O
H 2N
Rx-ID: 17553208 View in Reaxys 3/19 Yield
Conditions & References Reaction Steps: 2 1: 1.) NaOH, 2.) 4N aq. HCl / 1.) H2O, methanol, -3 deg C, 15 min 2: LiAlH4 / tetrahydrofuran / 2 h / Heating With hydrogenchloride, sodium hydroxide, lithium aluminium tetrahydride in tetrahydrofuran Cantrell, Amanda S.; Engelhardt, Per; Hoegberg, Marita; Jaskunas, S. Richard; Johansson, Nils Gunnar; Jordan, Christopher L.; Kangasmetsae, Jussi; Kinnick, Michael D.; Lind, Peter; Morin Jr., John M.; Muesing; Noreen, Rolf; Oeberg, Bo; Pranc, Paul; Sahlberg, Christer; Ternansky, Robert J.; Vasileff, Robert T.; Vrang, Lotta; West, Sarah J.; Zhang, Hong; Journal of Medicinal Chemistry; vol. 39; nb. 21; (1996); p. 4261 - 4274 View in Reaxys Reaction Steps: 4 1: pyridine; piperidine 2: sodium-amalgam 3: ammonia / 220 - 230 °C 4: sodium hypochlorite With piperidine, pyridine, sodium hypochlorite, sodium amalgam, ammonia Buck; Journal of the American Chemical Society; vol. 54; (1932); p. 3661,3662 View in Reaxys
O
O
O
O
HO
O
H 2N
Rx-ID: 21990676 View in Reaxys 4/19 Yield
Conditions & References Reaction Steps: 2 1: ammonia / 220 - 230 °C 2: sodium hypochlorite With sodium hypochlorite, ammonia Buck; Journal of the American Chemical Society; vol. 54; (1932); p. 3661,3662 View in Reaxys Reaction Steps: 3 1: benzene; sulfuric acid / unter Entfernen des entstehenden Wassers 2: amyl alcohol; hydrazine hydrate 3: beim Erwaermen des hergestellten Azids in Benzol und Erwaermen des Reaktionsprodukts mit wss. Salzsaeure With pentan-1-ol, sulfuric acid, hydrazine hydrate, benzene Leaf; Neuberger; Biochemical Journal; vol. 43; (1948); p. 606,608; Biochemical Journal; vol. 57; (1954); p. 528 View in Reaxys
O O HO
O
E
O
O
H 2N
Rx-ID: 21997586 View in Reaxys 5/19 Yield
Conditions & References Reaction Steps: 3 1: sodium-amalgam
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2: ammonia / 220 - 230 °C 3: sodium hypochlorite With sodium hypochlorite, sodium amalgam, ammonia Buck; Journal of the American Chemical Society; vol. 54; (1932); p. 3661,3662 View in Reaxys Reaction Steps: 4 1: Raney nickel; aq. NaOH solution / 73550.8 Torr / Hydrogenation 2: benzene; sulfuric acid / unter Entfernen des entstehenden Wassers 3: amyl alcohol; hydrazine hydrate 4: beim Erwaermen des hergestellten Azids in Benzol und Erwaermen des Reaktionsprodukts mit wss. Salzsaeure With sodium hydroxide, pentan-1-ol, sulfuric acid, nickel, hydrazine hydrate, benzene Leaf; Neuberger; Biochemical Journal; vol. 43; (1948); p. 606,608; Biochemical Journal; vol. 57; (1954); p. 528 View in Reaxys
O
O
H 2N
O
O
O
H 2N
Rx-ID: 379546 View in Reaxys 6/19 Yield
Conditions & References With sodium hypochlorite Buck; Journal of the American Chemical Society; vol. 54; (1932); p. 3661,3662 View in Reaxys 2H
2
H
2H 2H
O
O
E 2H 2H
O
N O
2
H
HCl
O
NH 2 2
H
2H
2H
2H
O 2H
Rx-ID: 11289582 View in Reaxys 7/19 Yield
Conditions & References
43 %
With lithium aluminium tetrahydride in tetrahydrofuran, Time= 24h, Heating Xu, Ya-Zhu; Chen, Chinpiao; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 49; nb. 13; (2006); p. 1187 - 1200 View in Reaxys
O
O
O
alkaline permanganate
O
O
H 2N
Rx-ID: 20403277 View in Reaxys 8/19 Yield
Conditions & References Reaction Steps: 2 1: ammonium acetate / 3 h / Heating 2: LiAlH4 / tetrahydrofuran / 4 h / Ambient temperature With ammonium acetate, lithium aluminium tetrahydride in tetrahydrofuran Kubo, Akinori; Saito, Naoki; Kawakami, Nanko; Matsuyama, Yasuo; Miwa, Teruyo; Synthesis; nb. 9; (1987); p. 824 - 827 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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O
O Cl
O
E
N
H
O
O
O
H 2N
Rx-ID: 11289583 View in Reaxys 9/19 Yield
Conditions & References With lithium aluminium tetrahydride in tetrahydrofuran, Time= 24h, Heating Xu, Ya-Zhu; Chen, Chinpiao; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 49; nb. 13; (2006); p. 1187 - 1200 View in Reaxys H
H 13C
H 13C 13CH O
13C
13CH
O
H 13C 13CH
13C
13C
13C
13C
O
13C
HCl
H H 2N
Rx-ID: 38014760 View in Reaxys 10/19 Yield
Conditions & References Reaction Steps: 6 1.1: N-bromosuccinmide / chloroform; N,N-dimethyl-formamide / 70 °C 2.1: copper(l) iodide; ethyl acetate / N,N-dimethyl-formamide; methanol / 48 h / 80 °C / |Sealed tube; |Inert atmosphere 3.1: titanium tetrachloride / dichloromethane / 17 h / -5 - 4 °C / |Inert atmosphere 4.1: ammonium acetate / 2 h / 70 °C 5.1: sodium tetrahydroborate; ethanol / ethyl acetate / 1 h / 22 °C 6.1: hydrogen; palladium 10 on activated carbon / methanol / 4 h 6.2: pH 3 With sodium tetrahydroborate, N-bromosuccinmide, copper(l) iodide, ethanol, palladium 10 on activated carbon, ammonium acetate, hydrogen, titanium tetrachloride, ethyl acetate in methanol, dichloromethane, chloroform, ethyl acetate, N,N-dimethyl-formamide, 3.1: |Rieche Formylation / 4.1: |Henry Nitro Aldol Condensation Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 57; nb. 5; (2014); p. 378 - 387 View in Reaxys H
H 13C 13CH HO
13C
13CH
H 13C 13CH
H 13C
13C
13
O
C
13
C
O
13 13C
C
HCl
H H 2N
Rx-ID: 38014781 View in Reaxys 11/19 Yield
Conditions & References Reaction Steps: 7 1.1: sodium hydroxide / water / 0.5 h / |Inert atmosphere 1.2: 1 h / 0 - 50 °C / |Inert atmosphere 2.1: N-bromosuccinmide / chloroform; N,N-dimethyl-formamide / 70 °C 3.1: copper(l) iodide; ethyl acetate / N,N-dimethyl-formamide; methanol / 48 h / 80 °C / |Sealed tube; |Inert atmosphere 4.1: titanium tetrachloride / dichloromethane / 17 h / -5 - 4 °C / |Inert atmosphere 5.1: ammonium acetate / 2 h / 70 °C 6.1: sodium tetrahydroborate; ethanol / ethyl acetate / 1 h / 22 °C 7.1: hydrogen; palladium 10 on activated carbon / methanol / 4 h 7.2: pH 3 With sodium tetrahydroborate, N-bromosuccinmide, copper(l) iodide, ethanol, palladium 10 on activated carbon, ammonium acetate, hydrogen, titanium tetrachloride, ethyl acetate, sodium hydroxide in methanol, dichloromethane, chloroform, water, ethyl acetate, N,N-dimethyl-formamide, 4.1: |Rieche Formylation / 5.1: |Henry Nitro Aldol Condensation
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Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 57; nb. 5; (2014); p. 378 - 387 View in Reaxys H
H
13
H C 13C
Br
13C
13
C H
H 13C
O
13
C
13CH
O
13C
13C
13C
13C
O
13C
HCl
H
H 2N
Rx-ID: 38014791 View in Reaxys 12/19 Yield
Conditions & References Reaction Steps: 5 1.1: copper(l) iodide; ethyl acetate / N,N-dimethyl-formamide; methanol / 48 h / 80 °C / |Sealed tube; |Inert atmosphere 2.1: titanium tetrachloride / dichloromethane / 17 h / -5 - 4 °C / |Inert atmosphere 3.1: ammonium acetate / 2 h / 70 °C 4.1: sodium tetrahydroborate; ethanol / ethyl acetate / 1 h / 22 °C 5.1: hydrogen; palladium 10 on activated carbon / methanol / 4 h 5.2: pH 3 With sodium tetrahydroborate, copper(l) iodide, ethanol, palladium 10 on activated carbon, ammonium acetate, hydrogen, titanium tetrachloride, ethyl acetate in methanol, dichloromethane, ethyl acetate, N,N-dimethyl-formamide, 2.1: |Rieche Formylation / 3.1: |Henry Nitro Aldol Condensation Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 57; nb. 5; (2014); p. 378 - 387 View in Reaxys
H C
H
13
H 13C O
13C
13C
H 13C
O
13C
13C
13
13CH
O
C
13
C
O
13 13C
C
HCl
H
H
H 2N
Rx-ID: 38014828 View in Reaxys 13/19 Yield
Conditions & References Reaction Steps: 4 1.1: titanium tetrachloride / dichloromethane / 17 h / -5 - 4 °C / |Inert atmosphere 2.1: ammonium acetate / 2 h / 70 °C 3.1: sodium tetrahydroborate; ethanol / ethyl acetate / 1 h / 22 °C 4.1: hydrogen; palladium 10 on activated carbon / methanol / 4 h 4.2: pH 3 With sodium tetrahydroborate, ethanol, palladium 10 on activated carbon, ammonium acetate, hydrogen, titanium tetrachloride in methanol, dichloromethane, ethyl acetate, 1.1: |Rieche Formylation / 2.1: |Henry Nitro Aldol Condensation Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 57; nb. 5; (2014); p. 378 - 387 View in Reaxys H
H
H 13C O
13C
13C
13C
H
13C 13C
H 13C
O O
O
13C
13C
13C
13C 13C
O HCl
H
H 2N
Rx-ID: 38014833 View in Reaxys 14/19 Yield
Conditions & References Reaction Steps: 3 1.1: ammonium acetate / 2 h / 70 °C 2.1: sodium tetrahydroborate; ethanol / ethyl acetate / 1 h / 22 °C 3.1: hydrogen; palladium 10 on activated carbon / methanol / 4 h 3.2: pH 3
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With sodium tetrahydroborate, ethanol, palladium 10 on activated carbon, ammonium acetate, hydrogen in methanol, ethyl acetate, 1.1: |Henry Nitro Aldol Condensation Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 57; nb. 5; (2014); p. 378 - 387 View in Reaxys H C
13
H 13C 13
O
C
O
13
C
H
H 13C
13 13
C H O
C
O
13C
13C
13C
13C
O
13C
HCl
H
N
H 2N
O
Rx-ID: 38014840 View in Reaxys 15/19 Yield
Conditions & References Reaction Steps: 2 1.1: sodium tetrahydroborate; ethanol / ethyl acetate / 1 h / 22 °C 2.1: hydrogen; palladium 10 on activated carbon / methanol / 4 h 2.2: pH 3 With sodium tetrahydroborate, ethanol, palladium 10 on activated carbon, hydrogen in methanol, ethyl acetate Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 57; nb. 5; (2014); p. 378 - 387 View in Reaxys H
H 13C O
13C
13C
13C
H O
O
13C
H
H 13C
13C
13C
13
O
C
N
13
C
13 13C
C
O HCl
H H 2N
O
Rx-ID: 38014843 View in Reaxys 16/19 Yield
Conditions & References
218 mg
Stage 1: With palladium 10 on activated carbon, hydrogen in methanol, Time= 4h Stage 2: With hydrogenchloride in methanol, pH= 3 Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 57; nb. 5; (2014); p. 378 - 387 View in Reaxys
O
O
O O
O O
H 2N
Rx-ID: 22015848 View in Reaxys 17/19 Yield
Conditions & References Reaction Steps: 2 1: amyl alcohol; hydrazine hydrate 2: beim Erwaermen des hergestellten Azids in Benzol und Erwaermen des Reaktionsprodukts mit wss. Salzsaeure With pentan-1-ol, hydrazine hydrate Leaf; Neuberger; Biochemical Journal; vol. 43; (1948); p. 606,608; Biochemical Journal; vol. 57; (1954); p. 528 View in Reaxys
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O
O
O H 2N
O
NH
O
H 2N
Rx-ID: 488020 View in Reaxys 18/19 Yield
Conditions & References beim Erwaermen des hergestellten Azids in Benzol und Erwaermen des Reaktionsprodukts mit wss. Salzsaeure Leaf; Neuberger; Biochemical Journal; vol. 43; (1948); p. 606,608; Biochemical Journal; vol. 57; (1954); p. 528 View in Reaxys
O
O H 2N
Rx-ID: 6590942 View in Reaxys 19/19 Yield
Conditions & References Patent; Polaroid Corp.; US3062884; (1955); ; vol. 58; nb. 5575d; (1963) View in Reaxys D. Similarly, replacing 3-methoxyphenethylamine with: 3,4-dimethoxyphenethylamine; 2,5-dimethoxyphenethylamine; 3,4-(ethylene-1,2-dioxy)phenethylamine; 2-methylphenethylamine; 3-methylphenethylamine; 4-methylphenethylamine; 3-ethylphenethylamine; 3,4-dimethylphenethylamine; 3-isobutylphenethylamine; ... Patent; Syntex (U.S.A.) Inc.; US5231181; (1993); (A1) English View in Reaxys
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