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Reactions (10)
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Targets (3)
Citations (8)
References
1
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Rx-ID: 5462854 Find similar reactions
entspr. Glyoxamid, LiAlH4;
Heinzelman; Szmuszkovicz
Progress in Drug Research, 1963 , vol. 6, p. 75,76-150 Chem.Abstr., 1964 , vol. 60, # 13215b Full Text View citing articles Show Details
With sodium methylate; sodium cyanoborohydride; acetic acid in methanol; water
T=20°C; pH=5 - 9; 2 h; Inert atmosphere; Hide Experimental Procedure
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
Patent: CN103601683 B, 2016 ; Location in patent: Paragraph 0106; 0108 ; Title/Abstract Full Text Show Details
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).
2
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Rx-ID: 30910241 Find similar reactions
94%
With sodium cyanoborohydride; acetic acid in methanol
T=0 - 20°C; Inert atmosphere; Hide Experimental Procedure
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Qu, Shi-Jin; Wang, Gui-Feng; Duan, Wen-Hu; Yao, Shan-Yan; Zuo, Jian-Ping; Tan, Chang-Heng; Zhu, Da-Yuan
Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 10 p. 3120 - 3127 Title/Abstract Full Text View citing articles Show Details
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.
3
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With lithium aluminium deuteride in tetrahydrofuran
Inert atmosphereMicrowave irradiation;
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Rx-ID: 28198066 Find similar reactions
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, 2008 , vol. 51, # 14 p. 423 - 429 Title/Abstract Full Text View citing articles Show Details
4
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Rx-ID: 11192121 Find similar reactions
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68%
With potassium carbonate in methanol
T=55°C; 120 h;
Wang, Yu-Yun; Chen, Chinpiao
Journal of the Chinese Chemical Society, 2007 , vol. 54, # 5 p. 1363 - 1368 Title/Abstract Full Text View citing articles Show Details
5
Synthesize Find similar Multi-step reaction with 4 steps 1: diethyl ether / 4 h / 0 - 20 °C 2: NH3 / CH2Cl2 / 0.5 h 3: 0.90 g / LiAlH4 / dioxane / 34 h / Heating 4: 68 percent / K2CO3 / methanol / 120 h / 55 °C View Scheme
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Rx-ID: 11300932 Find similar reactions
Wang, Yu-Yun; Chen, Chinpiao
Journal of the Chinese Chemical Society, 2007 , vol. 54, # 5 p. 1363 - 1368 Title/Abstract Full Text View citing articles Show Details
6
Synthesize Find similar Multi-step reaction with 3 steps 1: NH3 / CH2Cl2 / 0.5 h 2: 0.90 g / LiAlH4 / dioxane / 34 h / Heating 3: 68 percent / K2CO3 / methanol / 120 h / 55 °C View Scheme
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Rx-ID: 11321730 Find similar reactions
Wang, Yu-Yun; Chen, Chinpiao
Journal of the Chinese Chemical Society, 2007 , vol. 54, # 5 p. 1363 - 1368 Title/Abstract Full Text View citing articles Show Details
7
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Rx-ID: 11339369 Find similar reactions
8
Multi-step reaction with 2 steps 1: 0.90 g / LiAlH4 / dioxane / 34 h / Heating 2: 68 percent / K2CO3 / methanol / 120 h / 55 °C View Scheme
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Rx-ID: 9939934 Find similar reactions
46%
9
Wang, Yu-Yun; Chen, Chinpiao
Journal of the Chinese Chemical Society, 2007 , vol. 54, # 5 p. 1363 - 1368 Title/Abstract Full Text View citing articles Show Details
in diethyl ether
T=20°C; 16 h;
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Thiagaraj, Harish V.; Russo, Ethan B.; Burnett, Andrea; Goldstein, Eric; Thompson, Charles M.; Parker, Keith K.
Pharmacology, 2005 , vol. 74, # 4 p. 193 - 199 Title/Abstract Full Text View citing articles Show Details
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Rx-ID: 113803 Find similar reactions
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Vitali; Mossini
Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1959 , vol. 17, p. 84,86 Full Text View citing articles Show Details
10
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Rx-ID: 5462855 Find similar reactions
With tetrahydrofuran; lithium aluminium tetrahydride
Barlow; Khan
British Journal of Pharmacology and Chemotherapy, 1959 , vol. 14, p. 99,101 Full Text View citing articles Show Details