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14 reactions in Reaxys
2017-10-28 15h:04m:27s (EST)
NH
1. Query N
Search as: As drawn
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NH
N
Rx-ID: 5448634 View in Reaxys 1/14 Yield
Conditions & References Aminoalkohol 14c, NH3, Me. 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 entspr. Glyoxamid, LiAlH4 Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; ; vol. 60; nb. 13215b; (1964) View in Reaxys General procedure: under an argon atmosphere, the 200mg 5- hydroxy tryptamine hydrochloride (0.94 mmol) was dissolved in 10ml anhydrous methanol , The ice-cooling with stirring was added freshly prepared sodium methoxide (20mg Na was dissolved in anhydrous methanol 1ml) adjusting pH 8-9, Acetic acid was added followed by 0.22ml (3.76mmol) adjusting pH5-6, and then added 102mg sodium cyanoborohydride (1.88mmol), And finally 38percent aqueous formaldehyde solution was added dropwise 0.18ml (2.26mmol), the reaction temperature was raised toroom temperature, followed Stirring was continued for 2h (TLC detection progress of the reaction), the reactionwas complete, a solution of 2mol / L of Na pH 2 CO 3 solution was adjusted The reaction was terminated by 8-9,filtered and the filtrate (13ml) at 45 ° C and concentrated under reduced pressure, ice-water was added (25ml)diluted with n Butanol (30ml × 2) and the combined butanol extracts were concentrated divisible solvent.Water: methanol (volume ratio 4: 1)RP-18 column chromatography to give Compound QH-1 (164mg, yield85percent). With sodium methylate, sodium cyanoborohydride, acetic acid in methanol, water, Time= 2h, T= 20 °C , pH= 5 - 9, Inert atmosphere Patent; Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences,; TianjinChase Sun Pharmaceutical Co., Ltd; Zhu, Dayuan; Zuo, Jianping; Tan, Changheng; Qu, Shijin; Duan, Wenhu; Wang, Guifeng; Sun, Changhai; Yao, Xiaoqing; (44 pag.); CN103601683; (2016); (B) Chinese View in Reaxys
NH
NH O
N
NH 2
Rx-ID: 30910239 View in Reaxys 2/14 Yield 97 %
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
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View in Reaxys
NH 2H
O
2H
N 2H
O
2
H
N
NH
Rx-ID: 28198072 View in Reaxys 3/14 Yield
Conditions & References
78 %
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 2H
2H 2H 2H
2
H
NH
2H
2H
2H
2
H
2
H
N
2
I 2H
H
2H
2H
NH 2
2H
NH
Rx-ID: 11192120 View in Reaxys 4/14 Yield
Conditions & References
20 %
With potassium carbonate in methanol, Time= 120h, T= 45 - 50 °C Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368 View in Reaxys 2H
2H 2H 2H
2
H
2H
NH
(+-)-2-butyl-octan-1-ol
2
H
N
2H 2H
2H
NH
Rx-ID: 11300934 View in Reaxys 5/14 Yield
Conditions & References Reaction Steps: 4 1: diethyl ether / 4 h / 0 - 20 °C 2: NH3 / CH2Cl2 / 0.5 h 3: 0.90 g / LiAlH4 / dioxane / 34 h / Heating 4: 20 percent / K2CO3 / methanol / 120 h / 45 - 50 °C With lithium aluminium tetrahydride, ammonia, potassium carbonate in 1,4-dioxane, methanol, diethyl ether, dichloromethane Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368 View in Reaxys 2H
2H 2 H 2
2H
H
NH 2
H
2H
N
2H
O 2H
O
Cl
2H
NH
Rx-ID: 11321732 View in Reaxys 6/14
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Yield
Conditions & References Reaction Steps: 3 1: NH3 / CH2Cl2 / 0.5 h 2: 0.90 g / LiAlH4 / dioxane / 34 h / Heating 3: 20 percent / K2CO3 / methanol / 120 h / 45 - 50 °C With lithium aluminium tetrahydride, ammonia, potassium carbonate in 1,4-dioxane, methanol, dichloromethane Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368 View in Reaxys 2H
2H 2H 2H
2H
NH 2H
2H
NH 2 O
2H
N 2H
O
2H
NH
Rx-ID: 11339370 View in Reaxys 7/14 Yield
Conditions & References Reaction Steps: 2 1: 0.90 g / LiAlH4 / dioxane / 34 h / Heating 2: 20 percent / K2CO3 / methanol / 120 h / 45 - 50 °C With lithium aluminium tetrahydride, potassium carbonate in 1,4-dioxane, methanol Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368 View in Reaxys
NH
O
H N
O
N H N
Rx-ID: 9643021 View in Reaxys 8/14 Yield
Conditions & References Time= 9h, T= 180 °C Decker, Michael; Nguyen, Thi Thanh Huyen; Lehmann, Jochen; Tetrahedron; vol. 60; nb. 21; (2004); p. 4567 4578 View in Reaxys
NH
NH N H N
Br
Rx-ID: 113807 View in Reaxys 9/14 Yield
Conditions & References Vitali; Mossini; Bollettino Scientifico della Facolta di Chimica Industriale di Bologna; vol. 17; (1959); p. 84,86 View in Reaxys
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NH
NH
O O
N
N
Rx-ID: 294052 View in Reaxys 10/14 Yield
Conditions & References With lithium aluminium tetrahydride Nogradi; Monatshefte fuer Chemie; vol. 88; (1957); p. 768,776 View in Reaxys
NH
NH
N
Rx-ID: 22237353 View in Reaxys 11/14 Yield
Conditions & References Reaction Steps: 3 1: diethyl ether 2: H2O 3: LiAlH4 With lithium aluminium tetrahydride, diethyl ether, water Nogradi; Monatshefte fuer Chemie; vol. 88; (1957); p. 768,776 View in Reaxys
NH
NH
O N
O
Cl
Rx-ID: 22243519 View in Reaxys 12/14 Yield
Conditions & References Reaction Steps: 2 1: H2O 2: LiAlH4 With lithium aluminium tetrahydride, water Nogradi; Monatshefte fuer Chemie; vol. 88; (1957); p. 768,776 View in Reaxys
NH
O
NH
N
N
Rx-ID: 252136 View in Reaxys 13/14 Yield
Conditions & References With lithium aluminium tetrahydride Patent; Upjohn Co.; US2814625; (1954)
Copyright © 2017 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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View in Reaxys
NH
NH
O
N
Cl
Rx-ID: 22285648 View in Reaxys 14/14 Yield
Conditions & References Reaction Steps: 2 1: benzene 2: LiAlH4 With lithium aluminium tetrahydride, benzene Patent; Upjohn Co.; US2814625; (1954) View in Reaxys
Copyright © 2017 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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