Bioactivities (1672)
Yield
Reactions (14)
Substances (16)
Conditions
Targets (70)
Citations (14)
References
1
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With ammonia; lithium in tetrahydrofuran
T=-78 - -20°C; 1 h; Reagent/catalyst; Hide Experimental Procedure
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Rx-ID: 356231
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Satara Pharmaceuticals, LLC; Rajagopalan, Raghavan
Patent: US2016/89439 A1, 2016 ; Location in patent: Paragraph 0044 ; Title/Abstract Full Text Show Details
1:Example 1 General Procedure for the Reaction of the Excipient of Formulas I and II and Pseudoephedrine with Lithium in Liquid Ammonia
General procedure: Example 1 General Procedure for the Reaction of the Excipient of Formulas I and II and Pseudoephedrine with Lithium in Liquid Ammonia (0044) Lithium metal pieces (35 mg, 5.0 mmol) were carefully added to liquid ammonia (5-10 mL) at about −78° C. (dry ice, isopropyl alcohol). A dark blue solution began to form within a few seconds. The dark blue solution was stirred at −78° C. for about 3 to 5 minutes. Thereafter, a mixture of the excipient of Formula I (122-166 mg, 1.0 mmol) and pseudoephedrine (165 mg, 1.0 mmol) in anhydrous tetrahydrofuran (3 mL) was added to the dark blue solution. The entire reaction mixture was stirred while the temperature of the reaction was slowly raised to about −20° C. Stirring was continued at this temperature for about 1 hour. The reaction mixture was quenched with saturated ammonium chloride (2 mL) and water (3 mL), and diluted with methanol (5 mL). The reaction mixture was analyzed and quantified for the presence of methamphetamine. The results are given in Example 3 below. 1%
With acetylpyrazine; ammonia; lithium in tetrahydrofuran
T=-78 - -20°C; 1 h; Reagent/catalystTemperatureTime; Hide Experimental Procedure
DAYA DRUG DISCOVERIES, INC.; RAJAGOPALAN, Raghavan
Patent: WO2015/48597 A1, 2015 ; Location in patent: Page/Page column 9-10 ; Title/Abstract Full Text Show Details
1:
Example 1. General Procedure for the reaction of the exipient of Formulas I and II and pseudoephedrine with lithium in liquid ammonia. Lithium metal pieces (35 mg, 5.0 mmol) were carefully added to liquid ammonia (5-10 mL) at about -78 °C (dry ice, isopropyl alcohol). A dark blue solution began to form within a few seconds. The dark blue solution was stirred at -78 °C
for about 3 to 5 minutes. Thereafter, a mixture of the exipient of Formula I (122-166 mg, 1.0 mmol) and pseudoephedrine (165 mg, 1 .0 mmol) in anhydrous tetrahydrofuran (3 mL) was added to the dark blue solution. The entire reaction mixture was stirred while the temperature of the reaction was slowly raised to about - 20 °C. Stirring was continued at this temperature for about 1 hour. The reaction mixture was quenched with saturated ammonium chloride (2 mL) and water (3 mL), and diluted with methanol (5 mL). The reaction mixture was analyzed and quantified for the presence of methamphetamine. The results are given in Example 3 below. With phosphorus; hydrogen iodide
Ogata; zit. bei Emde
Helvetica Chimica Acta, 1929 , vol. 12, p. 373 Full Text View citing articles Show Details
2
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Rx-ID: 25930802
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With ammonia; lithium in tetrahydrofuran
T=-78°C; 0.0833333 h;
Matsumoto, Teruki; Urano, Yasuteru; Makino, Yukiko; Kikura-Hanajiri, Ruri; Kawahara, Nobuo; Goda, Yukihiro; Nagano, Tetsuo
Analytical Chemistry, 2008 , vol. 80, # 4 p. 1176 - 1181 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: hydrochlorid acid / methanol / 0.5 h / 760.05 Torr 2: palladium 10 on activated carbon; hydrogen / methanol / 16 h / 20 °C View Scheme
Lalwani, Komal G.; Sudalai, Arumugam
Tetrahedron Letters, 2015 , vol. 56, # 46 p. 6488 - 6490 Title/Abstract Full Text View citing articles Show Details
3
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With palladium 10 on activated carbon; hydrogen in methanol
T=20°C; 16 h; enantioselective reaction; Hide Experimental Procedure
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Rx-ID: 25930804
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Lalwani, Komal G.; Sudalai, Arumugam
Tetrahedron Letters, 2015 , vol. 56, # 46 p. 6488 - 6490 Title/Abstract Full Text View citing articles Show Details
(S)-N-methyl-1-phenylpropan-2-amine hydrochloride (4):
To a solution of ephedrine hydrochloride 1 (0.10 g, 6.2mmol) in methanolic HCl (10 mL) wasadded 10percent Pd/C (20 mg). The resulting solution was stirred under hydrogen (1 atmosphere) at 60 psi for 16 h at room temperature until disappearance of the starting compound as monitored by thin-layer chromatography (TLC). The reaction mixture was filtered through a celite pad to remove the catalyst, and the filtrate was concentrated in vacuo to get (S)-metamphetamine hydrochloride 4 as colorless solid (64 mg). 65%
With hydrochlorid acid; phosphorus
T=140°C; 4.5 h;
Matsumoto, Teruki; Urano, Yasuteru; Makino, Yukiko; Kikura-Hanajiri, Ruri; Kawahara, Nobuo; Goda, Yukihiro; Nagano, Tetsuo
Analytical Chemistry, 2008 , vol. 80, # 4 p. 1176 - 1181 Title/Abstract Full Text View citing articles Show Details
4
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Rx-ID: 25930803
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80%
Stage #1: With iodine; hypophosphorous acid
Heating; Stage #2: With sodium hydroxide in water
pH=> 10; Stage #3: With hydrogenchloride in toluene
David, Gabrielle E.; Hibbert, D. Brynn; Frew, Russell D.; Hayman, Alan R.
Australian Journal of Chemistry, 2010 , vol. 63, # 1 p. 22 - 29 Title/Abstract Full Text View citing articles Show Details
65%
With phosphorus; hydrogen iodide
T=140°C; 4.5 h;
Matsumoto, Teruki; Urano, Yasuteru; Makino, Yukiko; Kikura-Hanajiri, Ruri; Kawahara, Nobuo; Goda, Yukihiro; Nagano, Tetsuo
Analytical Chemistry, 2008 , vol. 80, # 4 p. 1176 - 1181 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 3 steps 1: sodium hydrogencarbonate / water / 12 h / 20 °C 2: Raney Ni / isopropyl alcohol / 50 - 55 °C / |Autoclave 3: hydrogenchloride / ethyl acetate / 20 h / 0 - 20 °C / |Large scale View Scheme
Pramanik, Chinmoy; Bapat, Kiran; Chaudhari, Ashok; Kulkarni, Mukund G.; Kolla, Rangarao; Sompalli, Srinivasarao; Tripathy, Narendra K.; Gurjar, Mukund K.
Organic Process Research and Development, 2014 , vol. 18, # 4 p. 495 - 500 Title/Abstract Full Text View citing articles Show Details
5
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Heating; Stage #2: With sodium hydroxide in water
pH=> 10; Stage #3: With hydrogenchloride in toluene
6
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Rx-ID: 29344283
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David, Gabrielle E.; Hibbert, D. Brynn; Frew, Russell D.; Hayman, Alan R.
Australian Journal of Chemistry, 2010 , vol. 63, # 1 p. 22 - 29 Title/Abstract Full Text View citing articles Show Details
Synthesize Find similar Stage #1: With phosphorus; water-d2
Heating; Stage #2: With sodium hydroxide in water
pH=> 10; Stage #3: With hydrogenchloride in toluene
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Rx-ID: 29344284
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David, Gabrielle E.; Hibbert, D. Brynn; Frew, Russell D.; Hayman, Alan R.
Australian Journal of Chemistry, 2010 , vol. 63, # 1 p. 22 - 29 Title/Abstract Full Text View citing articles Show Details
7
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Rx-ID: 588054
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With sulfuric acid; palladium; acetic acid
T=80°C; Hydrogenation;
Rosenmund; Karg
Chemische Berichte, 1942 , vol. 75, p. 1850,1856 Full Text View citing articles Show Details
Kindler; Hedemann; Schaerfe
Justus Liebigs Annalen der Chemie, 1948 , vol. 560, p. 215,219 Full Text View citing articles Show Details
With perchloric acid; palladium; acetic acid
T=60°C; Hydrogenation;
Rosenmund; Karg
Chemische Berichte, 1942 , vol. 75, p. 1850,1856 Full Text View citing articles Show Details
Kindler; Hedemann; Schaerfe
Justus Liebigs Annalen der Chemie, 1948 , vol. 560, p. 215,219 Full Text View citing articles Show Details
With thionyl chloride; palladium on barium sulfate; hydrogen; sodium acetate
1.) CHCl3, reflux, 3 h, 2.) AcOH; Yield given. Multistep reaction;
Noggle, F. Taylor; DeRuiter, Jack; Clark, C. Randall
Analytical Chemistry, 1986 , vol. 58, # 8 p. 1643 - 1648 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: thionyl chloride / CHCl3
2: H2 / Pd/C / ethanol View Scheme
Armellin, Silvia; Brenna, Elisabetta; Frigoli, Samuele; Fronza, Giovanni; Fuganti, Claudio; Mussida, Daniele
Analytical Chemistry, 2006 , vol. 78, # 9 p. 3113 - 3117 Title/Abstract Full Text View citing articles Show Details
8
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Rx-ID: 333846
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With phosphorus; hydrogen iodide
Ogata; zit. bei Emde
Helvetica Chimica Acta, 1929 , vol. 12, p. 373 Full Text View citing articles Show Details
With ammonia; lithium in water
Birch Reduction; Hide Experimental Procedure
GLOTELL PRODUCTS, INC.; BICKETT, Tim; EITER, Frank
Patent: WO2005/32458 A2, 2005 ; Location in patent: Page/Page column 32-33 ; Title/Abstract Full Text Show Details
1:
In a controlled laboratory setting, 12 microliters of the commercial product marketed AS"KEYACIDTM Rhodamine WT"and manufactured by Keystone Analine Corporation of Chicago, Illinois, which is a 21.2percent w/w solution of rhodamine WT in water, and 300 ML of anhydrous ammonia were combined in a flask. This is approximately equivalent to 2 oz OF KEYACID Rhodamine WT in one ton of liquid anhydrous ammonia. The mixture was stirred until a solution formed that had a very slight yellow tint. The solvation of rhodamine WT in ammonia transformed the rhodamine WT into a nearly colorless composition. The surface of each piece of equipment used in this process, however, was visibly stained a light pink in areas exposed to the ammonia and from which the ammonia had evaporated. The solution was also purposefully put in contact with various additional equipment and materials, including metal screwdriver heads, concrete, and paper. All exposed equipment and materials were visibly stained pink upon evaporation of the anhydrous ammonia. During the mixing process, some of the mixture unintentionally contacted items, including protective gloves and the hands of the researchers who were performing the mixing. These additional items were also visibly stained pink. [0071] The solution of dye in ammonia was added to 2 grams of pure pharmaceutical grade ephedrine in a 500 mL beaker. The contents of the flask were stirred to dissolve the ephedrine. Any material that came into contact with this solution, including the flask when the flask was emptied, was also visibly stained pink upon evaporation of the ammonia solvent. The visible pink stain on the flask was transferred to a sponge when the flask was washed. [0072] Lithium metal was added to the ephedrine solution. This mixture was heated to carry out a so-called"Birch"reaction. During the Birch reaction, materials contacted by the mixture were not stained. It is believed that the lack of a stain at this stage may be due to a reduction of the rhodamine WT to a colorless composition. [0073] Evaporation of the ammonia from the Birch reaction mixture left a free base form of methamphetamine. In order to purify it, the free base methamphetamine was dissolved into a liquid ether and converted to the hydrochloride salt by bubbling hydrogen chloride gas through the solution. The methamphetamine salt precipitated from solution. During this process plastic tubes used to carry the hydrogen chloride gas into the dissolved methamphetamine were visibly stained pink as was the beaker. [0074] The methamphetamine salt product was filtered through a coffee filter to retain the methamphetamine. The coffee filter used for this filtration along with the resultant product is shown in the picture of FIG. 3. Two things were observed. First, the coffee filter and resulting product are both stained pink. Further, the filtration does not occur easily because instead of a rapidly-drying, clear crystal being formed, the product was a pink sludge, which was difficult to filter and dry. This pink sludge (methamphetamine) visibly stained objects with which it came into contact pink, including plastic storage bags.
9
Synthesize Find similar Multi-step reaction with 2 steps 1: SOCl2
2: H2 / Pd/BaSO4
View Scheme
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Rx-ID: 12886381
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Kurashima, Naoki; Makino, Yukiko; Sekita, Setsuko; Urano, Yasuteru; Nagano, Tetsuo
Analytical Chemistry, 2004 , vol. 76, # 14 p. 4233 - 4236 Title/Abstract Full Text View citing articles Show Details
10
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With thionyl chloride; palladium on barium sulfate; hydrogen; sodium acetate
1.) CHCl3, reflux, 3 h, 2.) AcOH; Yield given. Multistep reaction;
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Rx-ID: 4260641
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Noggle, F. Taylor; DeRuiter, Jack; Clark, C. Randall
Analytical Chemistry, 1986 , vol. 58, # 8 p. 1643 - 1648 Title/Abstract Full Text View citing articles Show Details
11
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With thionyl chloride; palladium on barium sulfate; hydrogen; sodium acetate
1.) CHCl3, reflux, 3 h, 2.) AcOH; Yield given. Multistep reaction;
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Rx-ID: 4271306
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Noggle, F. Taylor; DeRuiter, Jack; Clark, C. Randall
Analytical Chemistry, 1986 , vol. 58, # 8 p. 1643 - 1648 Title/Abstract Full Text View citing articles Show Details
12
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With thionyl chloride; palladium on barium sulfate; hydrogen; sodium acetate
1.) CHCl3, reflux, 3 h, 2.) AcOH; Yield given. Multistep reaction;
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Rx-ID: 4271308
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Noggle, F. Taylor; DeRuiter, Jack; Clark, C. Randall
Analytical Chemistry, 1986 , vol. 58, # 8 p. 1643 - 1648 Title/Abstract Full Text View citing articles Show Details
13
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Yield given. Multistep reaction;
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Rx-ID: 2104711
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Buckley, Thomas F.; Rapoport, Henry
Journal of the American Chemical Society, 1981 , vol. 103, # 20 p. 6157 - 6163 Title/Abstract Full Text View citing articles Show Details
14
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T=80°C; Hydrogenation;
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Rx-ID: 588058
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Rosenmund; Karg
Chemische Berichte, 1942 , vol. 75, p. 1850,1856 Full Text View citing articles Show Details